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Yian Shi

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Name: Shi, Yian
Organization: Institute of Chemistry, Chinese Academy of Sciences , USA
Department:
Title: Professor(PhD)

TOPICS

An effective route to β2-amino acid derivatives via Pd-catalyzed regioselective hydrocarboxylation of 1,2-disubstituted enimides
Co-reporter:Jie Dai;Wenlong Ren;Wenju Chang;Ping Zhang
Organic Chemistry Frontiers 2017 vol. 4(Issue 2) pp:297-302
Publication Date(Web):2017/02/01
DOI:10.1039/C6QO00353B
An effective Pd(0)-catalyzed hydrocarboxylation of 1,2-disubstituted enimides with formic acid and HCOOPh is described. A variety of β2-amino acid derivatives are obtained in good yield with high regioselectivity without using external toxic CO gas.
A facile approach to ketones via Pd-catalyzed sequential carbonylation of olefins with formic acid
Co-reporter:Wenju Chang;Jie Dai;Jingfu Li;Yuan Shi;Wenlong Ren
Organic Chemistry Frontiers 2017 vol. 4(Issue 6) pp:1074-1078
Publication Date(Web):2017/05/31
DOI:10.1039/C7QO00111H
An effective palladium-catalyzed sequential carbonylation of olefins with formic acid is described. Ketones and the corresponding α,β-enones can be obtained with up to 90% yield. The reaction process is operationally simple and requires no toxic CO.
Catalytic enantioselective bromohydroxylation of aryl olefins with flexible functionalities
Co-reporter:Jing Li;Zequan Li;Xun Zhang;Bing Xu
Organic Chemistry Frontiers 2017 vol. 4(Issue 6) pp:1084-1090
Publication Date(Web):2017/05/31
DOI:10.1039/C6QO00636A
A highly enantioselective bromohydroxylation of aryl olefins with flexible functionalities has been achieved with (DHQD)2PHAL as a catalyst and H2O as a nucleophile, giving a variety of optically active bromohydrins with up to 98% ee. An acid additive has been found to be beneficial for the reactivity and enantioselectivity.
An Effective Pd-Catalyzed Regioselective Hydroformylation of Olefins with Formic Acid
Co-reporter:Wenlong Ren, Wenju Chang, Jie Dai, Yuan Shi, Jingfu Li, and Yian Shi
Journal of the American Chemical Society 2016 Volume 138(Issue 45) pp:14864-14867
Publication Date(Web):October 31, 2016
DOI:10.1021/jacs.6b10297
An effective palladium-catalyzed regioselective hydroformylation of olefins with formic acid is described. The ligand plays a crucial role in directing the reaction pathway. Linear aldehydes can be obtained in up to 93% yield with >20:1 regioselectivity using 1,3-bis(diphenylphosphino)propane (dppp) as the ligand. The reaction process is operationally simple and requires no syngas.
Palladium-Catalyzed Highly Regio- and Enantioselective Hydroesterification of Aryl Olefins with Phenyl Formate
Co-reporter:Jingfu Li, Wenju Chang, Wenlong Ren, Jie Dai, and Yian Shi
Organic Letters 2016 Volume 18(Issue 21) pp:5456-5459
Publication Date(Web):October 25, 2016
DOI:10.1021/acs.orglett.6b02467
An effective Pd-catalyzed regio- and enantioselective hydroesterification of aryl olefins with phenyl formate is described. A variety of phenyl 2-arylpropanoates can be obtained in good yields with high b/l ratios and ee’s without using toxic CO gas.
Phosphine Oxide–Sc(OTf)3 Catalyzed Highly Regio- and Enantioselective Bromoaminocyclization of (E)-Cinnamyl Tosylcarbamates. An Approach to a Class of Synthetically Versatile Functionalized Molecules
Co-reporter:Hongjie Pan, Hu Huang, Weigang Liu, Hua Tian, and Yian Shi
Organic Letters 2016 Volume 18(Issue 5) pp:896-899
Publication Date(Web):February 19, 2016
DOI:10.1021/acs.orglett.5b03459
A highly regio- and enantioselective bromoaminocyclization of (E)-cinnamyl tosylcarbamates catalyzed by a chiral phosphine oxide–Sc(OTf)3 complex is described. A wide variety of optically active aryl 5-bromo-1,3-oxazinan-2-ones can be obtained with high yield and enantioselectivity.
Total Synthesis of the Proposed Structure of Marineosin A
Co-reporter:Bing Xu, Guang Li, Jing Li, and Yian Shi
Organic Letters 2016 Volume 18(Issue 9) pp:2028-2031
Publication Date(Web):April 25, 2016
DOI:10.1021/acs.orglett.6b00632
A total synthesis of a proposed structure of marineosin A has been achieved. The key steps involve Lewis acid catalyzed spirocyclizaton, ring-closing metathesis, Paal–Knorr pyrrole synthesis, and a Vilsmeier–Haack type reaction with Tf2O.
Pd-Catalyzed regioselective hydroesterification of 2-allylphenols to seven-membered lactones without external CO gas
Co-reporter:Wenju Chang, Jingfu Li, Wenlong Ren and Yian Shi  
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 11) pp:3047-3052
Publication Date(Web):26 Jan 2016
DOI:10.1039/C5OB02663F
Effective Pd-catalyzed regioselective hydroesterification of 2-allylphenols with phenyl formate is described. A variety of seven-membered lactones can be obtained in good yields under mild conditions without the use of toxic CO gas.
A Facile Approach to Optically Active Hydroquinoline-2-carboxylates by a One-Pot Asymmetric Michael/Transamination/Cyclization Process
Co-reporter:Dr. Chao Rong;Hongjie Pan;Dr. Mao Liu;Hua Tian;Dr. Yian Shi
Chemistry - A European Journal 2016 Volume 22( Issue 9) pp:2887-2891
Publication Date(Web):
DOI:10.1002/chem.201503327

Abstract

An efficient one-pot synthesis of optically active hydroquinoline-2-carboxylates from 1,3-cyclohexanediones, β,γ-unsaturated α-keto ester, and benzylamine in the presence of a chiral base catalyst and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with good diastereoselectivity and high enantioselectivity is described. The reaction proceeds by a sequential asymmetric Michael/transamination/cyclization process.

Pd-Catalyzed Regiodivergent Hydroesterification of Aryl Olefins with Phenyl Formate
Co-reporter:Wenlong Ren, Wenju Chang, Yang Wang, Jingfu Li, and Yian Shi
Organic Letters 2015 Volume 17(Issue 14) pp:3544-3547
Publication Date(Web):July 2, 2015
DOI:10.1021/acs.orglett.5b01630
An effective Pd-catalyzed regiodivergent hydroesterification of aryl olefins with phenyl formate is described. Either linear or branched phenyl arylpropanoates can be obtained in good yields with high regioselectivities by the judicious choice of ligand without the use of toxic CO gas.
Enantioselective 6-exo-Bromoaminocyclization of Homoallylic N-Tosylcarbamates Catalyzed by a Novel Monophosphine-Sc(OTf)3 Complex
Co-reporter:Weigang Liu, Hongjie Pan, Hua Tian, and Yian Shi
Organic Letters 2015 Volume 17(Issue 16) pp:3956-3959
Publication Date(Web):July 17, 2015
DOI:10.1021/acs.orglett.5b01779
A highly enantioselective 6-exo-bromoaminocyclization of (E)-homoallylic N-tosylcarbamates catalyzed by a novel monophosphine-Sc(OTf)3 complex is described, giving a wide variety of optically active oxazinanones with high enantioselectivities.
Chiral Phosphine Oxide–Sc(OTf)3 Complex Catalyzed Enantioselective Bromoaminocyclization of 2-Benzofuranylmethyl N-Tosylcarbamates. Approach to a Novel Class of Optically Active Spiro Compounds
Co-reporter:Zequan Li and Yian Shi
Organic Letters 2015 Volume 17(Issue 23) pp:5752-5755
Publication Date(Web):November 16, 2015
DOI:10.1021/acs.orglett.5b02817
An efficient enantioselective bromoaminocyclization of 2-benzofuranylmethyl N-tosylcarbamates catalyzed by a chiral phosphine oxide–Sc(OTf)3 complex is described. A wide variety of optically active spiro benzofuran oxazolidinones can be obtained with high enantioselectivities.
An atom-economic approach to carboxylic acids via Pd-catalyzed direct addition of formic acid to olefins with acetic anhydride as a co-catalyst
Co-reporter:Yang Wang, Wenlong Ren and Yian Shi  
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 31) pp:8416-8419
Publication Date(Web):06 Jul 2015
DOI:10.1039/C5OB01180A
An effective Pd-catalyzed hydrocarboxylation of olefins using formic acid with acetic anhydride as a co-catalyst is described. A variety of carboxylic acids are obtained in good yields with high regioselectivities under mild reaction conditions without the use of toxic CO gas.
A palladium-catalyzed enantioselective hydroesterification of alkenylphenols with phenyl formate. A facile approach to optically active dihydrocoumarins
Co-reporter:Jingfu Li, Wenju Chang, Wenlong Ren, Wei Liu, Haining Wang and Yian Shi  
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 41) pp:10341-10347
Publication Date(Web):11 Aug 2015
DOI:10.1039/C5OB01431J
An effective palladium-catalyzed enantioselective hydroesterification of alkenylphenols with phenyl formate as a CO source is described. A variety of optically active dihydrocoumarins can be obtained in generally high yields with up to 91% ee.
A facile approach to β-amino acid derivatives via palladium-catalyzed hydrocarboxylation of enimides with formic acid
Co-reporter:Jie Dai, Wenlong Ren, Haining Wang and Yian Shi  
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 31) pp:8429-8432
Publication Date(Web):09 Jul 2015
DOI:10.1039/C5OB01304F
An effective Pd(0)-catalyzed hydrocarboxylation of enimides with formic acid in the presence of a catalytic amount of HCOOPh is described. A variety of β-amino acid derivatives are obtained in good yields with high regioselectivities without using external toxic CO gas.
Frontispiece: Catalytic Asymmetric Bromination of Unfunctionalized Olefins with H2O as a Nucleophile
Co-reporter:Dr. Xun Zhang;Dr. Jing Li;Hua Tian;Dr. Yian Shi
Chemistry - A European Journal 2015 Volume 21( Issue 33) pp:
Publication Date(Web):
DOI:10.1002/chem.201583361
Catalytic Asymmetric Bromination of Unfunctionalized Olefins with H2O as a Nucleophile
Co-reporter:Dr. Xun Zhang;Dr. Jing Li;Hua Tian;Dr. Yian Shi
Chemistry - A European Journal 2015 Volume 21( Issue 33) pp:11658-11663
Publication Date(Web):
DOI:10.1002/chem.201502133

Abstract

The dimeric cinchona alkaloid (DHQD)2PHAL is used to catalyze an effective asymmetric bromohydroxylation of unfunctionalized olefins with H2O as nucleophile an N-bromobenzamide as a bromine source. A variety of optically active bromohydrins are formed with up to 88 % ee.

Synthesis and Evaluation of 5,5′-Bitetralone-Based Chiral Phosphoric Acids
Co-reporter:Yazhou Wang; Wei Liu; Wenlong Ren
Organic Letters () pp:
Publication Date(Web):October 1, 2015
DOI:10.1021/acs.orglett.5b02400
A new type of phosphoric acid bearing a 5,5′-bitetralone scaffold was synthesized from BINOL and was shown to be a highly effective catalyst as illustrated in the asymmetric transfer hydrogenation of 2-phenylquinoline and the Friedel–Crafts reaction of 2,2,2-trifluoroacetophenone.
An effective route to β2-amino acid derivatives via Pd-catalyzed regioselective hydrocarboxylation of 1,2-disubstituted enimides
Co-reporter:Jie Dai, Wenlong Ren, Wenju Chang, Ping Zhang and Yian Shi
Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 2) pp:NaN302-302
Publication Date(Web):2016/11/03
DOI:10.1039/C6QO00353B
An effective Pd(0)-catalyzed hydrocarboxylation of 1,2-disubstituted enimides with formic acid and HCOOPh is described. A variety of β2-amino acid derivatives are obtained in good yield with high regioselectivity without using external toxic CO gas.
A facile approach to ketones via Pd-catalyzed sequential carbonylation of olefins with formic acid
Co-reporter:Wenju Chang, Jie Dai, Jingfu Li, Yuan Shi, Wenlong Ren and Yian Shi
Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 6) pp:NaN1078-1078
Publication Date(Web):2017/02/22
DOI:10.1039/C7QO00111H
An effective palladium-catalyzed sequential carbonylation of olefins with formic acid is described. Ketones and the corresponding α,β-enones can be obtained with up to 90% yield. The reaction process is operationally simple and requires no toxic CO.
Catalytic enantioselective bromohydroxylation of aryl olefins with flexible functionalities
Co-reporter:Jing Li, Zequan Li, Xun Zhang, Bing Xu and Yian Shi
Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 6) pp:NaN1090-1090
Publication Date(Web):2017/02/22
DOI:10.1039/C6QO00636A
A highly enantioselective bromohydroxylation of aryl olefins with flexible functionalities has been achieved with (DHQD)2PHAL as a catalyst and H2O as a nucleophile, giving a variety of optically active bromohydrins with up to 98% ee. An acid additive has been found to be beneficial for the reactivity and enantioselectivity.
An atom-economic approach to carboxylic acids via Pd-catalyzed direct addition of formic acid to olefins with acetic anhydride as a co-catalyst
Co-reporter:Yang Wang, Wenlong Ren and Yian Shi
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 31) pp:NaN8419-8419
Publication Date(Web):2015/07/06
DOI:10.1039/C5OB01180A
An effective Pd-catalyzed hydrocarboxylation of olefins using formic acid with acetic anhydride as a co-catalyst is described. A variety of carboxylic acids are obtained in good yields with high regioselectivities under mild reaction conditions without the use of toxic CO gas.
Pd-Catalyzed regioselective hydroesterification of 2-allylphenols to seven-membered lactones without external CO gas
Co-reporter:Wenju Chang, Jingfu Li, Wenlong Ren and Yian Shi
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 11) pp:NaN3052-3052
Publication Date(Web):2016/01/26
DOI:10.1039/C5OB02663F
Effective Pd-catalyzed regioselective hydroesterification of 2-allylphenols with phenyl formate is described. A variety of seven-membered lactones can be obtained in good yields under mild conditions without the use of toxic CO gas.
A facile approach to β-amino acid derivatives via palladium-catalyzed hydrocarboxylation of enimides with formic acid
Co-reporter:Jie Dai, Wenlong Ren, Haining Wang and Yian Shi
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 31) pp:NaN8432-8432
Publication Date(Web):2015/07/09
DOI:10.1039/C5OB01304F
An effective Pd(0)-catalyzed hydrocarboxylation of enimides with formic acid in the presence of a catalytic amount of HCOOPh is described. A variety of β-amino acid derivatives are obtained in good yields with high regioselectivities without using external toxic CO gas.
A palladium-catalyzed enantioselective hydroesterification of alkenylphenols with phenyl formate. A facile approach to optically active dihydrocoumarins
Co-reporter:Jingfu Li, Wenju Chang, Wenlong Ren, Wei Liu, Haining Wang and Yian Shi
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 41) pp:NaN10347-10347
Publication Date(Web):2015/08/11
DOI:10.1039/C5OB01431J
An effective palladium-catalyzed enantioselective hydroesterification of alkenylphenols with phenyl formate as a CO source is described. A variety of optically active dihydrocoumarins can be obtained in generally high yields with up to 91% ee.
An easy access to carboxylic acids via Pd-catalyzed hydrocarboxylation of olefins with HCOOLi as a CO surrogate under mild conditions
Co-reporter:Yang Wang, Yongming Zeng, Bangyu Yang and Yian Shi
Inorganic Chemistry Frontiers 2016 - vol. 3(Issue 9) pp:NaN1136-1136
Publication Date(Web):2016/07/18
DOI:10.1039/C6QO00187D
This paper describes an easy access to carboxylic acids via Pd-catalyzed hydrocarboxylation of olefins with HCOOLi and Ac2O under mild conditions without using external CO gas.
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