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Org Lett. 2004 Feb 5;6(3):377-80.

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

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1
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China.

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.

PMID:
14748597
DOI:
10.1021/ol036197s
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