Xiaobing Wan

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Name: 万小兵; XiaoBing Wan

Organization: Soochow University , China

Department: College of Chemistry

Title: Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

In Situ Generation of Quinolinium Ylides from Diazo Compounds: Copper-Catalyzed Synthesis of Indolizine

Co-reporter:Rongxiang Chen, Yanwei Zhao, Hongmei Sun, Ying Shao, Yudong Xu, Meihua Ma, Liang Ma, and Xiaobing Wan

The Journal of Organic Chemistry September 15, 2017 Volume 82(Issue 18) pp:9291-9291

Publication Date(Web):August 1, 2017

DOI:10.1021/acs.joc.7b01042

The Cu-catalyzed three-component reaction between quinolines, diazo compounds, and alkenes has been established for direct construction of indolizine derivatives via quinolinium ylides. This methodology is distinguished by the use of a commercially inexpensive catalyst and readily available starting materials, wide substrate scope, and operational simplicity.

Coupling Reaction of Cu-Based Carbene and Nitroso Radical: A Tandem Reaction To Construct Isoxazolines

Co-reporter:Rongxiang Chen, Yanwei Zhao, Shangwen Fang, Wenhao Long, Hongmei Sun, and Xiaobing Wan

Organic Letters November 3, 2017 Volume 19(Issue 21) pp:5896-5896

Publication Date(Web):October 16, 2017

DOI:10.1021/acs.orglett.7b02885

In this letter, an unprecedented cross-coupling reaction between copper carbene and nitroso radical has been developed. This radical-carbene coupling reaction (RCC reaction) offers a novel approach for the preparation of various isoxazolines, which features the construction of C–C, C–O, and C═N bonds in a one-pot process. The synthetic utility of our method is further enhanced by its mild reaction conditions, wide substrate scope, and simple procedures.

Cyanotrifluoromethylthiolation of Unactivated Olefins through Intramolecular Cyano Migration

Co-reporter:Meishan Ji;Zhen Wu;Jiajia Yu;Chen Zhu

Advanced Synthesis & Catalysis 2017 Volume 359(Issue 11) pp:1959-1962

Publication Date(Web):2017/06/06

DOI:10.1002/adsc.201700218

AbstractA new protocol for the elusive cyanotrifluoromethylthiolation of unactivated olefins is described. A broad range of vicinal CF3S-substituted alkyl nitriles are furnished in good yields under mild reaction conditions. The intramolecular cyano migration strategy is harnessed for the trifluoromethylthiolation of alkenes for the first time, thus offering an efficient tool for the construction of alkyl trifluoromethylthioethers.

Radical-carbene coupling reaction: Mn-catalyzed synthesis of indoles from aromatic amines and diazo compounds

Co-reporter:Huihuang Li;Yanwei Zhao;Liang Ma;Meihua Ma;Jun Jiang

Chemical Communications 2017 vol. 53(Issue 44) pp:5993-5996

Publication Date(Web):2017/05/30

DOI:10.1039/C7CC02440A

An unprecedented coupling reaction between aromatic amines and diazo compounds was well developed, which afforded a bridge connecting between radical chemistry and metal carbene chemistry. This Mn-catalyzed tandem reaction also provided a fundamentally different and practical approach to the indole skeleton under mild conditions.

Interception of amide ylides with sulfonamides: synthesis of (E)-N-sulfonyl amidines catalyzed by Zn(OTf)2

Co-reporter:Jijun Chen;Wenhao Long;Shangwen Fang;Yonggang Yang

Chemical Communications 2017 vol. 53(Issue 99) pp:13256-13259

Publication Date(Web):2017/12/12

DOI:10.1039/C7CC07364J

Through the interception of amide ylides with sulfonamides, we herein report the first general example of an intermolecular condensation reaction between sulfonamides and amides. Beyond formamides, this approach was successfully applied to a variety of lactams and linear amides, giving rise to a broad array of (E)-N-sulfonyl amidines.

Interception of amide ylides with sulfonamides: synthesis of (E)-N-sulfonyl amidines catalyzed by Zn(OTf)2

Co-reporter:Jijun Chen;Wenhao Long;Shangwen Fang;Yonggang Yang

Chemical Communications 2017 vol. 53(Issue 99) pp:13256-13259

Publication Date(Web):2017/12/12

DOI:10.1039/C7CC07364J

Bu4NI-Catalyzed Cross-Coupling between Sulfonyl Hydrazides and Diazo Compounds To Construct β-Carbonyl Sulfones Using Molecular Oxygen

Co-reporter:Yaxiong Wang, Liang Ma, Meihua Ma, Hao Zheng, Ying Shao, and Xiaobing Wan

Organic Letters 2016 Volume 18(Issue 19) pp:5082-5085

Publication Date(Web):September 20, 2016

DOI:10.1021/acs.orglett.6b02532

A new cross-coupling reaction between sulfonyl hydrazides and diazo compounds has been established, leading to a variety of β-carbonyl sulfones in good yields. This methodology was distinguished by simple manipulation, easily available starting materials, and wide substrate scope. A plausible mechanism involving a radical process was proposed based upon the experimental observations and literature.

A Cu-catalyzed four-component cascade reaction to construct β-ester-γ-amino ketones

Co-reporter:Jiayue Ling, Jie Zhang, Yanwei Zhao, Yudong Xu, Hanghang Wang, Yuanzheng Lv, Meishan Ji, Liang Ma, Meihua Ma and Xiaobing Wan

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 23) pp:5310-5316

Publication Date(Web):17 May 2016

DOI:10.1039/C6OB00873A

Herein, a novel Cu-catalyzed four-component cascade reaction, which encompasses styrenes, diazo compounds, amines, and tert-butyl hydroperoxide (TBHP), was developed for the synthesis of β-ester-γ-amino ketones. Mechanistically, this transformation was initiated by the interception of an electrophilic Cu-based carbene with nucleophilic α-aminoalkyl radicals, followed by a radical cascade process and an ionic Kornblum–DeLaMare reaction. The methodology was also distinguished by its wide substrate scope, easily available starting materials, and operational simplicity.

Difunctionalization of Styrenes with Perfluoroalkyl and tert-Butylperoxy Radicals: Room Temperature Synthesis of (1-(tert-Butylperoxy)-2-perfluoroalkyl)-ethylbenzene

Co-reporter:Erbo Shi, Jiajun Liu, Chunmei Liu, Ying Shao, Hanghang Wang, Yuanzheng Lv, Meishan Ji, Xiaoguang Bao, and Xiaobing Wan

The Journal of Organic Chemistry 2016 Volume 81(Issue 14) pp:5878-5885

Publication Date(Web):June 9, 2016

DOI:10.1021/acs.joc.6b00575

A novel strategy for the difunctionalization of styrenes was developed. This synthesis includes the use of electrophilic perfluoroalkyl and tert-butylperoxy radicals and produces (1-(tert-butylperoxy)-2-perfluoroalkyl)ethylbenzene at room temperature, which has been traditionally difficult to synthesize. With at least four radical species included in the transformation, its high chemoselectivity was extraordinary; the results were further elucidated using computational studies. The methodology also holds a good potential for application as a result of its mild reaction conditions, ease of further modification, and insensitivity to moisture and air.

Cu-Catalyzed Multicomponent Reaction of Styrenes, Perfluoroalkyl Halide, Alcohol, and tert-Butyl Hydroperoxide: One-Pot Synthesis of (Z)-β-Alkoxyperfluoroalkenone

Co-reporter:Qiang Luo, Chunmei Liu, Jingjing Tong, Ying Shao, Wenyu Shan, Hanghang Wang, Hao Zheng, Jiang Cheng, and Xiaobing Wan

The Journal of Organic Chemistry 2016 Volume 81(Issue 8) pp:3103-3111

Publication Date(Web):March 16, 2016

DOI:10.1021/acs.joc.5b02664

An efficient synthesis of Z-perfluoroalkyl-substituted enones by a multicomponent reaction strategy has been described. A variety of elusive perfluoroalkylated enones are furnished under mild reaction conditions in good yields with unique chemo- and stereoselectivity. A sequence of radical-mediated Kornblum–DeLaMare reaction, Michael addition, and HF elimination is proposed for the mechanism.

Corrigendum to “Metal free amide synthesis via carbon–carbon bond cleavage” [Tetrahedron 70 (2014) 9615–9620]

Co-reporter:Chunyin Zhu, Wei Wei, Peng Du, Xiaobing Wan

Tetrahedron 2016 Volume 72(Issue 5) pp:779

Publication Date(Web):4 February 2016

DOI:10.1016/j.tet.2015.12.033

Cu-based carbene involved in a radical process: a new crossover reaction to construct γ-peroxy esters and 1,4-dicarbonyl compounds

Co-reporter:Jiewen Jiang, Jiajun Liu, Ling Yang, Ying Shao, Jiang Cheng, Xiaoguang Bao and Xiaobing Wan

Chemical Communications 2015 vol. 51(Issue 79) pp:14728-14731

Publication Date(Web):10 Aug 2015

DOI:10.1039/C5CC05183E

Through merging Cu-based carbenes in a radical process, a novel crossover reaction has been successfully established, leading to the facile and efficient syntheses of various γ-peroxy esters and 1,4-dicarbonyl compounds. Considering that both Cu-based carbene complexes and radicals are extremely reactive, and therefore exist only in extraordinarily low concentrations, the high selectivity of this coupling reaction is unusual.

Combination of fluoroalkylation and Kornblum–DeLaMare reaction: a new strategy for the construction of (Z)-β-perfluoroalkyl enaminones

Co-reporter:Chunmei Liu, Erbo Shi, Feng Xu, Qiang Luo, Hongxiang Wang, Jijun Chen and Xiaobing Wan

Chemical Communications 2015 vol. 51(Issue 7) pp:1214-1217

Publication Date(Web):27 Nov 2014

DOI:10.1039/C4CC07833K

A novel strategy has been developed for the highly chemo- and stereo-selective synthesis of (Z)-β-perfluoroalkyl enaminones from readily available starting materials via a multicomponent radical reaction involving sequential fluoroalkylation and Kornblum–DeLaMare reaction. Notably, this methodology involves the concurrent cleavage of at least three chemical bonds, including two C–F bonds and one C–X (X = Br or I) bond, as well as the formation of three new bonds, including one CO bond, one CC bond and one C–N bond, in one pot.

Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP

Co-reporter:Jie Zhang, Ying Shao, Yaxiong Wang, Huihuang Li, Dongmei Xu and Xiaobing Wan

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 13) pp:3982-3987

Publication Date(Web):11 Feb 2015

DOI:10.1039/C5OB00109A

A transition-metal-free decarboxylation coupling process for the preparation of α-amino acid esters, which succeeded in merging hydrolysis/decarboxylation/nucleophilic substitution, is well described. This strategy uses commercially available inexpensive starting materials, catalysts and oxidants and has a wide substrate scope and operational simplicity.

Innentitelbild: Interception of Cobalt-Based Carbene Radicals with -Aminoalkyl Radicals: A Tandem Reaction for the Construction of -Ester--amino Ketones (Angew. Chem. 4/2015)

Co-reporter:Jie Zhang;Jiewen Jiang;Dongmei Xu;Qiang Luo;Hongxiang Wang;Jijun Chen;Huihuang Li;Yaxiong Wang ;Dr. Xiaobing Wan

Angewandte Chemie 2015 Volume 127( Issue 4) pp:

Publication Date(Web):

DOI:10.1002/ange.201411683

Inside Cover: Interception of Cobalt-Based Carbene Radicals with -Aminoalkyl Radicals: A Tandem Reaction for the Construction of -Ester--amino Ketones (Angew. Chem. Int. Ed. 4/2015)

Co-reporter:Jie Zhang;Jiewen Jiang;Dongmei Xu;Qiang Luo;Hongxiang Wang;Jijun Chen;Huihuang Li;Yaxiong Wang ;Dr. Xiaobing Wan

Angewandte Chemie International Edition 2015 Volume 54( Issue 4) pp:

Publication Date(Web):

DOI:10.1002/anie.201411683

Metal-Free Coupling of 2-Vinylphenols and Carboxylic Acids: An Access to 3-Acyloxy-2,3-dihydrobenzofurans

Co-reporter:Jijun Chen, Ying Shao, Hao Zheng, Jiang Cheng, and Xiaobing Wan

The Journal of Organic Chemistry 2015 Volume 80(Issue 21) pp:10734-10741

Publication Date(Web):October 12, 2015

DOI:10.1021/acs.joc.5b01941

A new coupling reaction between 2-vinylphenols and carboxylic acids was developed to synthesize 3-acyloxy-2,3-dihydrobenzofurans using Bu4NI as a catalyst and t-BuOOH as an oxidant. This simple and practical methodology is notable due to the ability to complete it under metal-free conditions, with easily available precursors, resulting in a product with high atom economy and high functional group tolerance. Upon the basis of experimental observations and literature, a plausible mechanism is proposed.

Interception of Cobalt-Based Carbene Radicals with -Aminoalkyl Radicals: A Tandem Reaction for the Construction of -Ester--amino Ketones

Co-reporter:Jie Zhang;Jiewen Jiang;Dongmei Xu;Qiang Luo;Hongxiang Wang;Jijun Chen;Huihuang Li;Yaxiong Wang ;Dr. Xiaobing Wan

Angewandte Chemie 2015 Volume 127( Issue 4) pp:1247-1251

Publication Date(Web):

DOI:10.1002/ange.201408874

Abstract

The interception of cobalt-based carbene radicals with α-aminoalkyl radicals was combined with the Kornblum–DeLaMare reaction and provides β-ester-γ-amino ketones, which are otherwise difficult to obtain in high chemoselectivity. Mechanistically, this transformation is an interplay of cobalt-based carbene radicals, organoradicals, and ionic intermediates and involves the construction of two CC bonds and one CO bond in a one-pot process. The reaction also features a wide substrate scope and is highly efficient and insensitive to moisture and air.

Interception of Cobalt-Based Carbene Radicals with -Aminoalkyl Radicals: A Tandem Reaction for the Construction of -Ester--amino Ketones

Co-reporter:Jie Zhang;Jiewen Jiang;Dongmei Xu;Qiang Luo;Hongxiang Wang;Jijun Chen;Huihuang Li;Yaxiong Wang ;Dr. Xiaobing Wan

Angewandte Chemie International Edition 2015 Volume 54( Issue 4) pp:1231-1235

Publication Date(Web):

DOI:10.1002/anie.201408874

Abstract

Co-Catalyzed Synthesis of 1,4-Dicarbonyl Compounds Using TBHP Oxidant

Co-reporter:Feng Zhang, Peng Du, Jijun Chen, Hongxiang Wang, Qiang Luo, and Xiaobing Wan

Organic Letters 2014 Volume 16(Issue 7) pp:1932-1935

Publication Date(Web):March 17, 2014

DOI:10.1021/ol5004687

A Co-catalyzed reaction for the construction of 1,4-dicarbonyls has been reported in which cascade organocobalt addition/trapping/Kornblum–DeLaMare rearrangement were involved. In view of the easy availability of starting materials, wide substrate scope, high functionality tolerance, and operational simplicity, this protocol constituted a simple, practical, and powerful alternative compared with previous approaches.

Dual Roles of Sulfonyl Hydrazides: A Three-Component Reaction To Construct Fully Substituted Pyrazoles Using TBAI/TBHP

Co-reporter:Jie Zhang, Ying Shao, Hongxiang Wang, Qiang Luo, Jijun Chen, Dongmei Xu, and Xiaobing Wan

Organic Letters 2014 Volume 16(Issue 12) pp:3312-3315

Publication Date(Web):June 9, 2014

DOI:10.1021/ol501312s

A mild and rapid approach has been developed for the construction of fully substituted pyrazoles using TBAI as a catalyst and TBHP as an oxidant, in which tosylhydrazide functions as the ring component and sulfonyl precursor. This protocol features a wide substrate scope with a broad range of functional group tolerance, utilizes easily available starting materials, can be scaled-up, and is operationally simple.

Radical–Polar Crossover Reactions: Oxidative Coupling of 1,3-Dioxolanes with Electron-Deficient Alkenes and Vinylarenes Based on a Radical Addition and Kornblum–DeLaMare Rearrangement

Co-reporter:Peng Du, Huihuang Li, Yaxiong Wang, Jiang Cheng, and Xiaobing Wan

Organic Letters 2014 Volume 16(Issue 24) pp:6350-6353

Publication Date(Web):December 4, 2014

DOI:10.1021/ol503128j

A new radical-polar crossover reaction has been developed involving the combination of a tandem radical reaction and Kornblum–DeLaMare rearrangement in a one-pot process. This simple methodology allows for the construction of polyfunctionalized carbonyl compounds via the oxidative coupling of 1,3-dioxolanes with electron-deficient alkenes and vinylarenes in the presence of Co(salen) and TBHP under mild conditions. This reaction also exhibited high functional group tolerance, wide substrate scope, and operational simplicity.

Metal free amide synthesis via carbon–carbon bond cleavage

Co-reporter:Chunyin Zhu, Wei Wei, Peng Du, Xiaobing Wan

Tetrahedron 2014 70(51) pp: 9615-9620

Publication Date(Web):

DOI:10.1016/j.tet.2014.11.003

A New Strategy for the Construction of α-Amino Acid Esters via Decarboxylation

Co-reporter:Jie Zhang, Jiewen Jiang, Yuling Li, Yun Zhao, and Xiaobing Wan

Organic Letters 2013 Volume 15(Issue 13) pp:3222-3225

Publication Date(Web):June 19, 2013

DOI:10.1021/ol401139m

A new α-amino acid esters formation reaction has been developed via decarboxylation. The methodology is distinguished by its practical novelty in terms of the readily accessible starting materials, environmentally benign reaction conditions and waste streams, and wide substrate scope.

Ruthenium-catalyzed oxidation of alkynes to 1,2-diketones under room temperature and one-pot synthesis of quinoxalines

Co-reporter:Yuan Xu, Xiaobing Wan

Tetrahedron Letters 2013 Volume 54(Issue 7) pp:642-645

Publication Date(Web):13 February 2013

DOI:10.1016/j.tetlet.2012.11.142

A ruthenium-catalyzed alkyne oxidation to 1,2-diketones using Oxone under room temperature is reported. Both substrate scope and mechanism were discussed. Notably, combination of the alkyne oxidation and condensation cyclization in one pot offers a very efficient and convenient entry into quinoxaline derivatives.

Iodide-Catalyzed Synthesis of N-Nitrosamines via C–N Cleavage of Nitromethane

Co-reporter:Jie Zhang, Jiewen Jiang, Yuling Li, and Xiaobing Wan

The Journal of Organic Chemistry 2013 Volume 78(Issue 22) pp:11366-11372

Publication Date(Web):October 15, 2013

DOI:10.1021/jo401915t

An iodide-catalyzed process to synthesize N-nitrosamines has been developed using TBHP as the oxidant. The mild catalytic system succeeded in cleaving the carbon–nitrogen bond in nitromethane. This methodology uses commercially available, inexpensive catalysts and oxidants and has a wide substrate scope and operational simplicity.

Nucleophilic Attack of -Aminoalkyl Radicals on CarbonNitrogen Triple Bonds to Construct -Amino Nitriles: An Experimental and Computational Study

Co-reporter:Chao Zhang;Chunmei Liu;Ying Shao;Dr. Xiaoguang Bao;Dr. Xiaobing Wan

Chemistry - A European Journal 2013 Volume 19( Issue 52) pp:17917-17925

Publication Date(Web):

DOI:10.1002/chem.201303296

Abstract

A new reactivity pattern of α-aminoalkyl radicals, involving nucleophilic attack on CN triple bonds under thermal conditions, has been developed to construct α-amino nitriles. In contrast to previous CH functionalization of tertiary amines involving α-aminoalkyl radicals, this methodology does not require the use of photocatalytic conditions or a transition-metal catalyst. Inexpensive and nontoxic phenylacetonitrile was chosen as cyano source for this α-aminonitrile forming reaction. A plausible mechanism is proposed based upon experimental and computational results. An α-aminoalkyl radical intermediate and benzoyl cyanide have been shown to be key intermediates in this green and mild radical process. Nucleophilic attack of the α-aminoalkyl radical on the CN bond of PhCOCN followed by an elimination step forms the desired α-aminonitrile and an acyl radical.

Tetrabutylammonium Iodide Catalyzed Synthesis of Allylic Ester with tert-Butyl Hydroperoxide as an Oxidant

Co-reporter:Erbo Shi, Ying Shao, Shulin Chen, Huayou Hu, Zhaojun Liu, Jie Zhang, and Xiaobing Wan

Organic Letters 2012 Volume 14(Issue 13) pp:3384-3387

Publication Date(Web):June 25, 2012

DOI:10.1021/ol3013606

A metal-free C–H oxidation for the construction of allylic esters has been developed. The use of a commercially available and inexpensive catalyst and oxidant, and readily available starting materials, coupled with the operational simplicity of the reaction, renders the methodology a useful alternative to other approaches typically employed in the synthesis of allylic esters.

Coupling of Methyl Ketones and Primary or Secondary Amines Leading to α-Ketoamides

Co-reporter:Wei Wei, Ying Shao, Huayou Hu, Feng Zhang, Chao Zhang, Yuan Xu, and Xiaobing Wan

The Journal of Organic Chemistry 2012 Volume 77(Issue 17) pp:7157-7165

Publication Date(Web):August 9, 2012

DOI:10.1021/jo301117b

A metal-free oxidative coupling of methyl ketones and primary or secondary amines to α-ketoamides has been developed. Four intermediates, α-iodoketone, α-aminoketone, iminium intermediate, and α-hydroxy amine have been identified through a series of control experiments. The atom-economic methodology can be scaled-up, tolerates a variety of functional groups, and is operationally simple.

Cross Coupling of Acyl and Aminyl Radicals: Direct Synthesis of Amides Catalyzed by Bu4NI with TBHP as an Oxidant

Co-reporter:Zhaojun Liu;Jie Zhang;Shulin Chen;Erbo Shi;Yuan Xu;Dr. Xiaobing Wan

Angewandte Chemie International Edition 2012 Volume 51( Issue 13) pp:3231-3235

Publication Date(Web):

DOI:10.1002/anie.201108763

Cross Coupling of Acyl and Aminyl Radicals: Direct Synthesis of Amides Catalyzed by Bu4NI with TBHP as an Oxidant

Co-reporter:Zhaojun Liu;Jie Zhang;Shulin Chen;Erbo Shi;Yuan Xu;Dr. Xiaobing Wan

Angewandte Chemie 2012 Volume 124( Issue 13) pp:3285-3289

Publication Date(Web):

DOI:10.1002/ange.201108763

Synthesis of tert-butyl peresters from aldehydes by Bu4NI-catalyzed metal-free oxidation and its combination with the Kharasch–Sosnovsky reaction

Co-reporter:Wei Wei, Chao Zhang, Yuan Xu and Xiaobing Wan

Chemical Communications 2011 vol. 47(Issue 38) pp:10827-10829

Publication Date(Web):24 Aug 2011

DOI:10.1039/C1CC14602E

A new tert-butyl peresters synthesis directly from aldehydes and TBHP was developed viaBu4NI-catalyzed aldehyde C−H oxidation. Mechanistic studies suggest that the protocol proceeds via a radical process. Combining the method with the Kharasch–Sosnovsky reaction offers a practical approach for the synthesis of allylic esters from simple aldehydes and alkenesvia a two-step one-pot procedure.

Ru-catalyzed aerobic oxidative coupling of arylboronic acids with arenes

Co-reporter:Hong Li, Wei Wei, Yuan Xu, Chao Zhang and Xiaobing Wan

Chemical Communications 2011 vol. 47(Issue 5) pp:1497-1499

Publication Date(Web):16 Nov 2010

DOI:10.1039/C0CC04322B

A Ru-catalyzed oxidative coupling of arenes with boronic acids using molecular oxygenvia direct C–H activation is reported. Both the scope and the mechanism of the process are discussed.

Ruthenium-Catalyzed Oxidation of Alkenes at Room Temperature: A Practical and Concise Approach to α-Diketones

Co-reporter:Shulin Chen, Zhaojun Liu, Erbo Shi, Long Chen, Wei Wei, Hong Li, Yannan Cheng, and Xiaobing Wan

Organic Letters 2011 Volume 13(Issue 9) pp:2274-2277

Publication Date(Web):April 13, 2011

DOI:10.1021/ol200716d

The catalytic oxidation of alkenes to α-diketones is unprecedented. A new oxidation of alkenes, catalyzed by a ruthenium complex, which allows an efficient route to α-diketones using TBHP as an oxidant is described. This methodology is highly functional group tolerant, is practically convenient, requires no additional ligand, and operates under mild conditions with short reaction times. Based upon experimental observations, a plausible mechanism is proposed.

Synthesis of arylketones by ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids

Co-reporter:Hong Li, Yuan Xu, Erbo Shi, Wei Wei, Xiangqiang Suo and Xiaobing Wan

Chemical Communications 2011 vol. 47(Issue 27) pp:7880-7882

Publication Date(Web):10 Jun 2011

DOI:10.1039/C1CC12843D

The first ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids is reported. Various aliphatic and aromatic aldehydes are transformed to the corresponding arylketones. A total of 31 examples with moderate to excellent yields are presented, together with the results of an initial mechanistic investigation.

Bu4NI-Catalyzed CO Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction

Co-reporter:Long Chen;Erbo Shi;Zhaojun Liu;Shulin Chen;Wei Wei;Hong Li;Kai Xu;Dr. Xiaobing Wan

Chemistry - A European Journal 2011 Volume 17( Issue 15) pp:4085-4089

Publication Date(Web):

DOI:10.1002/chem.201100192

Ruthenium-Catalyzed Alkyne Oxidation with Part-Per-Million Catalyst Loadings

Co-reporter:Wei Ren;Jinfeng Liu;Long Chen

Advanced Synthesis & Catalysis 2010 Volume 352( Issue 9) pp:1424-1428

Publication Date(Web):

DOI:10.1002/adsc.201000250

Abstract

Using a catalytic system of the (cymene)ruthenium dichloride dimer, [Ru(cymene)Cl₂]₂, (0.001 mol%) and iodine (10 mol%), a variety of alkynes bearing different functional groups were oxidized with tert-butyl hydroperoxide (TBHP; 70% solution in water) under mild conditions to give 1,2-diketones in good to excellent yields. Two noteworthy features of the method are the extremely high catalyst productivity (TON up to 420,000) and scale-up to 1 mol. Preliminary mechanism investigations showed that iodonium ion and water were involved in the transformation.

Wacker-Type Oxidation of Alkynes into 1,2-Diketones Using Molecular Oxygen

Co-reporter:Wei Ren, Yuanzhi Xia, Shun-Jun Ji, Yong Zhang, Xiaobing Wan and Jing Zhao

Organic Letters 2009 Volume 11(Issue 8) pp:1841-1844

Publication Date(Web):March 25, 2009

DOI:10.1021/ol900344g

An intriguing new Wacker-type oxidation of alkynes catalyzed by PdBr2 and CuBr2 is described, which opens an efficient access to 1,2-diketones using molecular oxygen. Under the optimized conditions, a variety of alkynes, including diarylalkynes, arylalkylalkynes, and dialkylalkynes, were compatible substrates in this transformation. The mechanism of this reaction was preliminarily investigated by control experiments.

Combination of fluoroalkylation and Kornblum–DeLaMare reaction: a new strategy for the construction of (Z)-β-perfluoroalkyl enaminones

Co-reporter:Chunmei Liu, Erbo Shi, Feng Xu, Qiang Luo, Hongxiang Wang, Jijun Chen and Xiaobing Wan

Chemical Communications 2015 - vol. 51(Issue 7) pp:NaN1217-1217

Publication Date(Web):2014/11/27

DOI:10.1039/C4CC07833K

Synthesis of arylketones by ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids

Co-reporter:Hong Li, Yuan Xu, Erbo Shi, Wei Wei, Xiangqiang Suo and Xiaobing Wan

Chemical Communications 2011 - vol. 47(Issue 27) pp:NaN7882-7882

Publication Date(Web):2011/06/10

DOI:10.1039/C1CC12843D

Ru-catalyzed aerobic oxidative coupling of arylboronic acids with arenes

Co-reporter:Hong Li, Wei Wei, Yuan Xu, Chao Zhang and Xiaobing Wan

Chemical Communications 2011 - vol. 47(Issue 5) pp:NaN1499-1499

Publication Date(Web):2010/11/16

DOI:10.1039/C0CC04322B

A Ru-catalyzed oxidative coupling of arenes with boronic acids using molecular oxygenvia direct C–H activation is reported. Both the scope and the mechanism of the process are discussed.

Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP

Co-reporter:Jie Zhang, Ying Shao, Yaxiong Wang, Huihuang Li, Dongmei Xu and Xiaobing Wan

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 13) pp:NaN3987-3987

Publication Date(Web):2015/02/11

DOI:10.1039/C5OB00109A

A Cu-catalyzed four-component cascade reaction to construct β-ester-γ-amino ketones

Co-reporter:Jiayue Ling, Jie Zhang, Yanwei Zhao, Yudong Xu, Hanghang Wang, Yuanzheng Lv, Meishan Ji, Liang Ma, Meihua Ma and Xiaobing Wan

Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 23) pp:NaN5316-5316

Publication Date(Web):2016/05/17

DOI:10.1039/C6OB00873A

Synthesis of tert-butyl peresters from aldehydes by Bu4NI-catalyzed metal-free oxidation and its combination with the Kharasch–Sosnovsky reaction

Co-reporter:Wei Wei, Chao Zhang, Yuan Xu and Xiaobing Wan

Chemical Communications 2011 - vol. 47(Issue 38) pp:NaN10829-10829

Publication Date(Web):2011/08/24

DOI:10.1039/C1CC14602E

Cu-based carbene involved in a radical process: a new crossover reaction to construct γ-peroxy esters and 1,4-dicarbonyl compounds

Co-reporter:Jiewen Jiang, Jiajun Liu, Ling Yang, Ying Shao, Jiang Cheng, Xiaoguang Bao and Xiaobing Wan

Chemical Communications 2015 - vol. 51(Issue 79) pp:NaN14731-14731

Publication Date(Web):2015/08/10

DOI:10.1039/C5CC05183E

Radical-carbene coupling reaction: Mn-catalyzed synthesis of indoles from aromatic amines and diazo compounds

Co-reporter:Huihuang Li, Yanwei Zhao, Liang Ma, Meihua Ma, Jun Jiang and Xiaobing Wan

Chemical Communications 2017 - vol. 53(Issue 44) pp:NaN5996-5996

Publication Date(Web):2017/05/10

DOI:10.1039/C7CC02440A

In situ generation of nitrilium from nitrile ylide and the subsequent Mumm rearrangement: copper-catalyzed synthesis of unsymmetrical diacylglycine esters

Co-reporter:Jijun Chen, Ying Shao, Liang Ma, Meihua Ma and Xiaobing Wan

Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 45) pp:NaN10732-10732

Publication Date(Web):2016/10/27

DOI:10.1039/C6OB02037B

A novel in situ generation of nitrilium from a nitrile ylide and the subsequent Mumm rearrangement of carboxylic acid, nitrile, and diazo compounds gave various unsymmetrical diacylglycine esters in moderate to high yields. This copper-catalyzed cascade reaction enables one-pot generation of two C–N bonds, one CO bond, and one C–H bond, with nitrogen as the only byproduct. The reaction has a broad functional-group tolerance, is rapid, easily scales up to the 100 mmol scale, and is insensitive to air and moisture.

[3 + 2] cycloaddition and subsequent oxidative dehydrogenation between alkenes and diazo compounds: a simple and direct approach to pyrazoles using TBAI/TBHP

Co-reporter:Ying Shao, Jingjing Tong, Yanwei Zhao, Hao Zheng, Liang Ma, Meihua Ma and Xiaobing Wan

Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 36) pp:NaN8492-8492

Publication Date(Web):2016/08/15

DOI:10.1039/C6OB01522K

A novel Bu4NI-catalyzed pyrazole formation reaction is well described via sequential [3 + 2] cycloaddition and oxidative dehydrogenation reactions using TBHP as the primary oxidant. In comparison with previous cases toward pyrazoles from alkenes and diazo compounds, alkenes without a pre-organized leaving group were applied in this transformation. In addition, this methodology was distinguished by its broad substrate scope, commercially available inexpensive starting materials, high atom economy and operational simplicity.