Literature DB >> 19248070

Elementary steps of gold catalysis: NMR spectroscopy reveals the highly cationic character of a "gold carbenoid".

Günter Seidel1, Richard Mynott, Alois Fürstner.   

Abstract

What are you? Even though the metal-induced ring opening of 3,3-disubstituted cyclopropenes is known to serve as a genuine carbene generator, the use of Au(I) in this reaction leads to a reactive intermediate with highly cationic character. This result has important implications for gold catalysis in general, which in the past has been commonly attributed to the intervention of gold carbenes.

Entities:  

Year:  2009        PMID: 19248070     DOI: 10.1002/anie.200806059

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  27 in total

1.  Mechanistic surprises in the gold(I)-catalyzed intramolecular hydroarylation of allenes.

Authors:  Dieter Weber; Michael A Tarselli; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Gold catalysis: Carbene or cation?

Authors:  Antonio M Echavarren
Journal:  Nat Chem       Date:  2009-09       Impact factor: 24.427

3.  Umpolung reactivity of indole through gold catalysis.

Authors:  Biao Lu; Yingdong Luo; Lianzhu Liu; Longwu Ye; Yanzhao Wang; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-14       Impact factor: 15.336

4.  A Brief Survey of our Contribution to Stable Carbene Chemistry.

Authors:  David Martin; Mohand Melaimi; Michele Soleilhavoup; Guy Bertrand
Journal:  Organometallics       Date:  2011-09-22       Impact factor: 3.876

5.  Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes.

Authors:  Z Jane Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

6.  Enantioselective cyclizations of silyloxyenynes catalyzed by cationic metal phosphine complexes.

Authors:  Jean-François Brazeau; Suyan Zhang; Ignacio Colomer; Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2012-01-31       Impact factor: 15.419

Review 7.  Stable cyclic carbenes and related species beyond diaminocarbenes.

Authors:  Mohand Melaimi; Michèle Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

8.  Tempering the reactivities of postulated α-oxo gold carbenes using bidentate ligands: implication of tricoordinated gold intermediates and the development of an expedient bimolecular assembly of 2,4-disubstituted oxazoles.

Authors:  Yingdong Luo; Kegong Ji; Yuxue Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2012-10-11       Impact factor: 15.419

9.  Serendipitous discovery of the catalytic hydroammoniumation and methylamination of alkynes.

Authors:  Xiaoming Zeng; Rei Kinjo; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

10.  A bonding model for gold(I) carbene complexes.

Authors:  Diego Benitez; Nathan D Shapiro; Ekaterina Tkatchouk; Yiming Wang; William A Goddard; F Dean Toste
Journal:  Nat Chem       Date:  2009-09       Impact factor: 24.427

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