Literature DB >> 15932319

A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones.

Silvia Díez-González1, Harneet Kaur, Fabiano Kauer Zinn, Edwin D Stevens, Steven P Nolan.   

Abstract

The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC.HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.

Entities:  

Year:  2005        PMID: 15932319     DOI: 10.1021/jo050397v

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  12 in total

1.  Application of a C2-symmetric copper carbenoid in the enantioselective hydrosilylation of dialkyl and aryl-alkyl ketones.

Authors:  Abigail Albright; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2011-11-16       Impact factor: 15.419

2.  Chemoselective hydrosilylation of hydroxyketones.

Authors:  Marta L Lage; Scott J Bader; Kanicha Sa-Ei; John Montgomery
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

3.  Design and synthesis of C2-symmetric N-heterocyclic carbene precursors and metal carbenoids.

Authors:  Abigail Albright; Daniel Eddings; Regina Black; Christopher J Welch; Nikolay N Gerasimchuk; Robert E Gawley
Journal:  J Org Chem       Date:  2011-08-25       Impact factor: 4.354

4.  NHC-catalyzed dehydrogenative self-coupling of diphenylsilane: A facile synthesis of octaphenylcyclotetra(siloxane).

Authors:  Abigail Albright; Robert E Gawley
Journal:  Tetrahedron Lett       Date:  2011-11-16       Impact factor: 2.415

5.  Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.

Authors:  Zachary A Buchan; Scott J Bader; John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Sugar Silanes: Versatile Reagents for Stereocontrolled Glycosylation via Intramolecular Aglycone Delivery.

Authors:  Jordan T Walk; Zachary A Buchan; John Montgomery
Journal:  Chem Sci       Date:  2015-06-01       Impact factor: 9.825

7.  Copper(I) complexes of mesoionic carbene: structural characterization and catalytic hydrosilylation reactions.

Authors:  Stephan Hohloch; Fenja Leena Duecker; Margarethe van der Meer; Biprajit Sarkar
Journal:  Molecules       Date:  2015-04-22       Impact factor: 4.411

8.  The Simplified Human Intestinal Microbiota (SIHUMIx) Shows High Structural and Functional Resistance against Changing Transit Times in In Vitro Bioreactors.

Authors:  Stephanie Serena Schäpe; Jannike Lea Krause; Beatrice Engelmann; Katarina Fritz-Wallace; Florian Schattenberg; Zishu Liu; Susann Müller; Nico Jehmlich; Ulrike Rolle-Kampczyk; Gunda Herberth; Martin von Bergen
Journal:  Microorganisms       Date:  2019-12-03

9.  Copper diamidocarbene complexes: characterization of monomeric to tetrameric species.

Authors:  Lee R Collins; John P Lowe; Mary F Mahon; Rebecca C Poulten; Michael K Whittlesey
Journal:  Inorg Chem       Date:  2014-02-11       Impact factor: 5.165

10.  A general synthetic route to [Cu(X)(NHC)] (NHC = N-heterocyclic carbene, X = Cl, Br, I) complexes.

Authors:  Orlando Santoro; Alba Collado; Alexandra M Z Slawin; Steven P Nolan; Catherine S J Cazin
Journal:  Chem Commun (Camb)       Date:  2013-11-18       Impact factor: 6.222

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