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Synfacts 2014; 10(1): 0083
DOI: 10.1055/s-0033-1340361
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Terminal Olefin Synthesis via Reaction of Aldehydes with Allylsamarium Bromide

Contributor(s):
Paul Knochel
,
Christoph Sämann
Li Y, Hu Y.-Y, Zhang S.-L * Soochow University, Suzhou, P. R. of China
Dual Role of Allylsamarium Bromide as a Grignard Reagent and a Single Electron Transfer Reagent in the One-Pot Synthesis of Terminal Olefins.

Chem. Commun. 2013;
49: 10635-10637
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

terminal olefines - aromatic aldehydes - samarium

Significance

A simple and efficient one-pot protocol for the synthesis of terminal alkenes has been reported. The reaction of carbonyl compounds with allylsamarium bromide in the presence of diethyl phosphate furnishes the corresponding olefins in good to excellent yields.


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Comment

Allylsamarium bromide acts in the reported reaction as both, a nucleophilic reagent and a single electron transfer reagent. Moreover, the described methodology is very versatile since several functional groups are tolerated.


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