Steven P. Nolan

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Organization: University of St Andrews
Department: EaStCHEM School of Chemistry
Title:
Co-reporter:Danila Gasperini;Dr. Alba Collado;Dr. Adrián Goméz-Suárez;Dr. David B. Cordes;Dr. Alexra M. Z. Slawin;Dr. Steven P. Nolan
Chemistry - A European Journal 2015 Volume 21( Issue 14) pp:5403-5412
Publication Date(Web):
DOI:10.1002/chem.201406543

Abstract

A new synthetic strategy was devised leading to the formation of complexes, such as [Au(IPr)(CH2COCH3)]. The approach capitalizes on the formation of a decomposition product observed in the course of the synthesis of [Au(IPr)(Cl)]. A library of gold acetonyl complexes containing the most common N-heterocyclic carbene (NHC) ligands has been synthesized. These acetonyl complexes are good synthons for the preparation of numerous organogold complexes. Moreover, they have proven to be precatalysts in common gold(I)-catalyzed reactions.

Co-reporter:Adrián Gómez-Suárez, Yoshihiro Oonishi, Sebastien Meiries, and Steven P. Nolan
Organometallics 2013 Volume 32(Issue 4) pp:1106-1111
Publication Date(Web):February 6, 2013
DOI:10.1021/om301249r
The synthesis of a series of digold hydroxide complexes is reported. These diaurated species, of the formula [{Au(NHC)}2(μ-OH)][BF4] (where NHC = IPrCl, IPr*, IPent), were easily prepared via the cationic species [Au(NHC)(NCCH3)][BF4] in aqueous media. The catalytic activity of these novel complexes was tested and compared to that of the previously reported IPr and SIPr derivatives. These digold hydroxide species are highly active in water-inclusive organic transformations, such as the alkyne and nitrile hydration reactions, and the Meyer–Schuster rearrangement. One salient feature of these systems is the lack of any additive to induce catalytic activity.
Co-reporter:Silvia Díez-González, Nicolas Marion and Steven P. Nolan
Chemical Reviews 2009 Volume 109(Issue 8) pp:3612
Publication Date(Web):July 9, 2009
DOI:10.1021/cr900074m
Co-reporter:Sylvain Gaillard, Xavier Bantreil, Alexandra M. Z. Slawin and Steven P. Nolan  
Dalton Transactions 2009 (Issue 35) pp:6967-6971
Publication Date(Web):26 Jun 2009
DOI:10.1039/B907109A
The compounds 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene silver chloride [AgCl(IPrMe)] 3 and 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(I) chloride [AuCl(IPrMe)] 4 have been synthesized. The attempted synthesis of the corresponding 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(III) chloride by oxidative addition of chlorine gas on 4 allowed for the formation of the expected complex, concomitantly with 6, resulting from a chlorination of a methyl group situated in the backbone of the NHC (N-heterocyclic carbene). Additionally, the buried volume %Vbur of the IPrMe ligand in [AgCl(IPrMe)] 3 and [AuCl(IPrMe)] 4 complexes was calculated and compared to %Vbur of more classical NHCs. This quantification of the steric hinderance of the IPrMe ligand reveals the influence of the substituent modulation in the backbone of NHCs.
Co-reporter:Hervé Clavier;Fréderic Caijo;Etienne Borré;Diane Rix;Fabien Boeda;Marc Mauduit
European Journal of Organic Chemistry 2009 Volume 2009( Issue 25) pp:4254-4265
Publication Date(Web):
DOI:10.1002/ejoc.200900407

Abstract

The synthesis and characterization of three novel trifluoromethylamido-containing “boomerang” precatalysts bearing various N-heterocyclic carbene (NHC) ligands are reported. Comparative kinetic and stability studies show the significant effect of the NHC on the catalyst reaction profile. An investigation of the reaction scope for diverse metathesis transformations has allowed us to establish the influence of the NHC on catalyst activity, especially as a function of substrate steric bulk. The excellent stability of one of the novel precatalysts is disclosed, and allowed for its recovery at the end of catalytic reactions. Large-scale ring-closing metathesis, enyne-metathesis and cross-metathesis experiments have revealed the recoverability of the catalyst. ICP-MS analyses of the synthesized products reveal Ru contamination levels of less than 2.5 ppm.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Co-reporter:Hervé Clavier;Andrea Correa;Luigi Cavallo;Eduardo C. Escudero-Adán;Jordi Benet-Buchholz;Alexra M. Z. Slawin
European Journal of Inorganic Chemistry 2009 Volume 2009( Issue 13) pp:
Publication Date(Web):
DOI:10.1002/ejic.200900292

No abstract is available for this article.

Co-reporter:Hervé Clavier;Andrea Correa;Luigi Cavallo;Eduardo C. Escudero-Adán;Jordi Benet-Buchholz;Alexra M. Z. Slawin
European Journal of Inorganic Chemistry 2009 Volume 2009( Issue 13) pp:1767-1773
Publication Date(Web):
DOI:10.1002/ejic.200801235

Abstract

Complexes of palladium bearing NHC ligands (NHC=N-heterocyclic carbene) were synthesized and fully characterized. The [Pd(NHC)(allyl)Cl] series was obtained by simple cleavage of [Pd(allyl)Cl]2 by using either the isolated free NHC or the in situ generated NHC. The NHC ligand sterics were varied by introduction of groups attached to the C4–C5 carbon atoms of the NHC backbone. Results of the X-ray diffraction study permitted determination of the NHC steric parameters within this series. It was observed that the NHC backbone induces variations in its percent buried volume (%Vbur) as a function of the N-substituents.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Co-reporter:Serena Fantasia Dr.;JonathanD. Egbert;Václav Jur&x10d;ík Dr.;CatherineS.J. Cazin Dr.;Heiko Jacobsen Dr.;Luigi Cavallo Dr.;D.Michael Heinekey Dr.;StevenP. Nolan Dr.
Angewandte Chemie International Edition 2009 Volume 48( Issue 28) pp:5182-5186
Publication Date(Web):
DOI:10.1002/anie.200900463
Co-reporter:Nicolas Marion Dr.;Gilles Lemière;Andrea Correa;Chiara Costabile;RubénS. Ramón;Xavier Moreau Dr.;Pierre deFrémont Dr.;Rim Dahmane;Alexra Hours Dr.;Denis Lesage;Jean-Claude Tabet Dr.;Jean-Philippe Goddard Dr.;Vincent Gon Dr.;Luigi Cavallo Dr.;Louis Fensterbank Dr.;Max Malacria Dr.;StevenP. Nolan Dr.
Chemistry - A European Journal 2009 Volume 15( Issue 13) pp:3243-3260
Publication Date(Web):
DOI:10.1002/chem.200801387
Co-reporter:RubénS. Ramón;Nicolas Marion Dr.;StevenP. Nolan Dr.
Chemistry - A European Journal 2009 Volume 15( Issue 35) pp:8695-8697
Publication Date(Web):
DOI:10.1002/chem.200901231
Co-reporter:Hervé Clavier, César A. Urbina-Blanco and Steven P. Nolan
Organometallics 2009 Volume 28(Issue 9) pp:2848-2854
Publication Date(Web):March 25, 2009
DOI:10.1021/om900071t
The synthesis and characterization of a novel indenylidene-containing ruthenium catalyst bearing the N-heterocyclic carbene (NHC) ligand 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene (SIPr) are reported. Comparative reactivity studies with other indenylidene complexes using various substrates show the importance of the sterically demanding SIPr ligand on catalyst reaction profile. The investigation of the reaction scope for ring-closing metathesis transformations establishes the influence of the NHC on catalyst activity especially as a function of substrate steric bulk. The novel catalyst was found very efficient at room temperature for nonsterically hindered substrates. Since the new catalyst was found to be soluble in a variety of solvents, a number of these were examined to gauge the importance of solvent effects.
Co-reporter:Rubén S. Ramón, Nicolas Marion, Steven P. Nolan
Tetrahedron 2009 65(9) pp: 1767-1773
Publication Date(Web):
DOI:10.1016/j.tet.2008.10.111
Co-reporter:Sylvain Gaillard, Xavier Bantreil, Alexandra M. Z. Slawin and Steven P. Nolan
Dalton Transactions 2009(Issue 35) pp:NaN6971-6971
Publication Date(Web):2009/06/26
DOI:10.1039/B907109A
The compounds 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene silver chloride [AgCl(IPrMe)] 3 and 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(I) chloride [AuCl(IPrMe)] 4 have been synthesized. The attempted synthesis of the corresponding 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(III) chloride by oxidative addition of chlorine gas on 4 allowed for the formation of the expected complex, concomitantly with 6, resulting from a chlorination of a methyl group situated in the backbone of the NHC (N-heterocyclic carbene). Additionally, the buried volume %Vbur of the IPrMe ligand in [AgCl(IPrMe)] 3 and [AuCl(IPrMe)] 4 complexes was calculated and compared to %Vbur of more classical NHCs. This quantification of the steric hinderance of the IPrMe ligand reveals the influence of the substituent modulation in the backbone of NHCs.