Rhodium-Catalyzed Reaction of Terminal Alkynes with Allylamine Leading to (E)-3-Alkylidene N-Heterocycles

Terminal alkynes react with allylamine in the presence of a RhCl(PPh3)3 catalyst to give (E)-3-alkylidene-3,4-dihydro-2H-pyrroles. The products consist of two molecules of alkyne and one molecule of allylamine. Although dimers, trimers, and oligomers of alkynes are also obtained as byproducts, the a...

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Bibliographic Details
Published in:Organic letters 2006-09, Vol.8 (20), p.4641-4643
Main Authors: Fukumoto, Yoshiya, Kinashi, Fuyuko, Kawahara, Takuya, Chatani, Naoto
Format: Article
Language:English
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Summary:Terminal alkynes react with allylamine in the presence of a RhCl(PPh3)3 catalyst to give (E)-3-alkylidene-3,4-dihydro-2H-pyrroles. The products consist of two molecules of alkyne and one molecule of allylamine. Although dimers, trimers, and oligomers of alkynes are also obtained as byproducts, the addition of various ammonium salts to the reaction suppresses such oligomerization, resulting in an increase in product.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0619415