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Transition-metal-catalyzed formation of trans alkenes via coupling of aldehydes.

Authors
Type
Published Article
Journal
Organic Letters
1523-7052
Publisher
American Chemical Society
Publication Date
Volume
6
Issue
3
Pages
377–380
Identifiers
PMID: 14748597
Source
Medline
License
Unknown

Abstract

[reaction: see text] Rh(2)(OAc)(4) catalyzed the formation of exclusively trans fluorinated alkenes from aldehydes and pentafluorobenzaldehyde tosylhydrazone salts, which were readily prepared from pentafluorobenzaldehyde using the Bamford-Stevens reaction. A series of pentafluorophenyl-containing alkenes were synthesized from aldehydes in moderate to good yields under mild reaction conditions in a one-pot reaction. It is the first report of coupling two different aldehydes to form exclusively trans alkenes.

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