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Mercury-Free Preparation and Selective Reactions of Propargyl (and Propargylic) Grignard Reagents

ZnBr2 was found to catalyze formation of propargyl and propargylic Grignard reagents, and thus put an end to the standard method using a mercury catalyst. The Grignard reagents were submitted to addition reaction with carbonyl compounds and allylation with the cyclic monoacetate to afford the propar...

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Bibliographic Details
Published in:Organic letters 2007-08, Vol.9 (18), p.3535-3538
Main Authors: Acharya, Hukum P, Miyoshi, Kei, Kobayashi, Yuichi
Format: Article
Language:English
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Summary:ZnBr2 was found to catalyze formation of propargyl and propargylic Grignard reagents, and thus put an end to the standard method using a mercury catalyst. The Grignard reagents were submitted to addition reaction with carbonyl compounds and allylation with the cyclic monoacetate to afford the propargyl-type products selectively. Furthermore, the product from the monoacetate was transformed to an acetylene analogue of 2-(5,6-epoxyisoprostane A2)phosphorylcholines.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol071397f