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

Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes. Research Abstract Details 

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Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes. Abstract Text:

Vincent Lavallo,Guido D Frey,Shazia Kousar,Bruno Donnadieu,Guy Bertrand,

Addition of a sterically demanding cyclic (alkyl)(amino)carbene (CAAC) to AuCl(SMe(2)) followed by treatment with [Et(3)Si(Tol)](+)[B(C(6)F(5))(4)](-) in toluene affords the isolable [(CAAC)Au(eta(2)-toluene)](+)[B(C(6)F(5))(4)](-) complex. This cationic Au(I) complex efficiently mediates the catalytic coupling of enamines and terminal alkynes to yield allenes and not propargyl amines as observed with other catalysts. Mono-, di-, and tri-substituted enamines can be used, as well as aryl-, alkyl-, and trimethylsilyl-substituted terminal alkynes. The reaction tolerates sterically hindered substrates and is diastereoselective. This general catalytic protocol directly couples two unsaturated carbon centers to form the three-carbon allenic core. The reaction most probably proceeds through an unprecedented "carbene/vinylidene cross-coupling."

Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes. Publishing Authors By Initials

V Lavallo,GD Frey,S Kousar,B Donnadieu,G Bertrand,

For similar organic chemicals: hydrocarbons: hydrocarbons, acyclic: alkenes: vinyl compounds research abstracts see: organic chemicals: hydrocarbons: hydrocarbons, acyclic: alkenes: vinyl compounds research

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Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Proceedings of the National Academy of Sciences of

VOLUME: 104

Page Numbers: 13569-73

Journal Abbreviation: Proc. Natl. Acad. Sci. U.S.A.

ISSN: 0027-8424

DAY: 13

MONTH: 08

YEAR: 2007

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

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LANGUAGE: eng

NlmUniqueID: 7505876

Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes. Keywords Mesh Terms:

KEYWORDS: Vinyl Compounds

MESH TERMS: chemistry

Chemical & Substance for Abstract: Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes. Information

Substance Name: Gold

Registry Number: 7440-57-5

Grant and Affiliation Information for Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes.

AFFILIATION: University of California Riverside-Centre National de la Recherche Scientifique Joint Research Chemistry Laboratory (Unité Mixte Internationale 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: R01 GM68825

ACRONYM: GM

MEDLINETA: Proc Natl Acad Sci U S A

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