Gold catalysis: Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond

A. Stephen K. Hashmi; Tobias Häffner; Weibo Yang; Sreekumar Pankajakshan; Sascha Schäfer; Lara Schultes; Frank Rominger; Wolfgang Frey

doi:10.1002/chem.201200306

Gold catalysis: Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond

A. Stephen K. Hashmi, Tobias Häffner, Weibo Yang, Sreekumar Pankajakshan, Sascha Schäfer, Lara Schultes, Frank Rominger, Wolfgang Frey

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

It takes al-kynes: The formation of furyl-substituted heterocycles from furanynes with donor groups on the furan-alkyne tether and mechanistic control experiments indicate the involvement of open-chained carbenium ions in the overall insertion of an alkyne into a C-C bond, rather than the usual spirocyclic intermediates (see scheme).

Original language	English (US)
Pages (from-to)	10480-10486
Number of pages	7
Journal	Chemistry - A European Journal
Volume	18
Issue number	34
DOIs	https://doi.org/10.1002/chem.201200306
State	Published - Aug 20 2012

Keywords

alkynes
carbocations
furans
gold
heterocycles
reaction mechanisms

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

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10.1002/chem.201200306

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T2 - Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond

AU - Hashmi, A. Stephen K.

AU - Häffner, Tobias

AU - Yang, Weibo

AU - Pankajakshan, Sreekumar

AU - Schäfer, Sascha

AU - Schultes, Lara

AU - Rominger, Frank

AU - Frey, Wolfgang

PY - 2012/8/20

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N2 - It takes al-kynes: The formation of furyl-substituted heterocycles from furanynes with donor groups on the furan-alkyne tether and mechanistic control experiments indicate the involvement of open-chained carbenium ions in the overall insertion of an alkyne into a C-C bond, rather than the usual spirocyclic intermediates (see scheme).

AB - It takes al-kynes: The formation of furyl-substituted heterocycles from furanynes with donor groups on the furan-alkyne tether and mechanistic control experiments indicate the involvement of open-chained carbenium ions in the overall insertion of an alkyne into a C-C bond, rather than the usual spirocyclic intermediates (see scheme).

KW - alkynes

KW - carbocations

KW - furans

KW - gold

KW - heterocycles

KW - reaction mechanisms

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Gold catalysis: Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond

Abstract

Keywords

ASJC Scopus subject areas

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