Synthesis 2005(11): 1901-1905  
DOI: 10.1055/s-2004-834920
PSP
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Synthesis of Terminal Alkenes

Valérie Paquet, Hélène Lebel*
Département de Chimie, Université de Montréal, Montréal, Québec, H3C 3J7, Canada
Fax: +1(514)3432177; e-Mail: [email protected];
Further Information

Publication History

Received 5 October 2004
Publication Date:
24 November 2004 (online)

Abstract

Terminal alkenes have been efficiently prepared via a rhodium-catalyzed olefination procedure using Wilkinson’s catalyst in the presence of triphenylphosphine, 2-propanol and trimethylsilyldiazomethane. Optimized reaction conditions are described for aldehydes and ketones, as well as alternative work up procedures.

    References

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  • 11b

    As trimethylsilyldiazomethane is non-explosive and non-mutagenic, the very careful operations used for the preparation of diazomethane are not necessary.

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10

Some bottles purchased from Aldrich contain as much as 50% of chloromethyltrimethylsilane by 1H NMR.

13

See ref. 11 for analytical procedure.