Literature DB >> 19219866

A cationic gold(I) complex as a general catalyst for the intermolecular hydroamination of alkynes: application to the one-pot synthesis of allenes from two alkynes and a sacrificial amine.

Xiaoming Zeng1, Guido D Frey, Shazia Kousar, Guy Bertrand.   

Abstract

Two very distinct chemical reactions, yet a single catalyst: A gold complex promotes the formation of tertiary enamines from a variety of terminal and internal alkynes. Subsequent addition of a terminal alkyne to the reaction mixture affords allenes (see scheme).

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Year:  2009        PMID: 19219866      PMCID: PMC2790055          DOI: 10.1002/chem.200802626

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  36 in total

Review 1.  Asymmetric hydroamination of non-activated carbon-carbon multiple bonds.

Authors:  Isabelle Aillaud; Jacqueline Collin; Jérôme Hannedouche; Emmanuelle Schulz
Journal:  Dalton Trans       Date:  2007-09-07       Impact factor: 4.390

2.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

Review 3.  Hydroamination: direct addition of amines to alkenes and alkynes.

Authors:  Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal:  Chem Rev       Date:  2008-08-26       Impact factor: 60.622

4.  Homogeneous catalytic hydroamination of alkynes and allenes with ammonia.

Authors:  Vincent Lavallo; Guido D Frey; Bruno Donnadieu; Michele Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Recent developments in enantioselective gold(I) catalysis.

Authors:  Ross A Widenhoefer
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

6.  Intramolecular "hydroiminiumation and -amidiniumation" of alkenes: a convenient, flexible, and scalable route to cyclic iminium and imidazolinium salts.

Authors:  Rodolphe Jazzar; Jean-Baptiste Bourg; Rian D Dewhurst; Bruno Donnadieu; Guy Bertrand
Journal:  J Org Chem       Date:  2007-04-05       Impact factor: 4.354

7.  Gold(III) porphyrin-catalyzed cycloisomerization of allenones.

Authors:  Cong-Ying Zhou; Philip Wai Hong Chan; Chi-Ming Che
Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

8.  Titanium hydrazido and imido complexes: synthesis, structure, reactivity, and relevance to alkyne hydroamination.

Authors:  Yahong Li; Yanhui Shi; Aaron L Odom
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419

9.  Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes.

Authors:  Vincent Lavallo; Guido D Frey; Shazia Kousar; Bruno Donnadieu; Guy Bertrand
Journal:  Proc Natl Acad Sci U S A       Date:  2007-08-13       Impact factor: 11.205

10.  A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water.

Authors:  Chunmei Wei; Chao-Jun Li
Journal:  J Am Chem Soc       Date:  2003-08-13       Impact factor: 15.419

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  7 in total

1.  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

Review 2.  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

Review 3.  Recent Advances in the Domain of Cyclic (Alkyl)(Amino) Carbenes.

Authors:  Saroj Kumar Kushvaha; Ankush Mishra; Herbert W Roesky; Kartik Chandra Mondal
Journal:  Chem Asian J       Date:  2022-02-26

4.  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

5.  Synthesis of a simplified version of stable bulky and rigid cyclic (alkyl)(amino)carbenes, and catalytic activity of the ensuing gold(I) complex in the three-component preparation of 1,2-dihydroquinoline derivatives.

Authors:  Xiaoming Zeng; Guido D Frey; Rei Kinjo; Bruno Donnadieu; Guy Bertrand
Journal:  J Am Chem Soc       Date:  2009-06-24       Impact factor: 15.419

6.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

7.  Fullerene C60 promoted photochemical hydroamination reactions of an electron deficient alkyne with trimethylsilyl group containing tertiary N-alkylbenzylamines.

Authors:  Suk Hyun Lim; Hannara Jang; Dae Won Cho
Journal:  RSC Adv       Date:  2021-02-03       Impact factor: 3.361

  7 in total

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