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A practical method for the synthesis of 2-alkynylpropenals.

ABSTRACT: A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation. Critical to the success of this approach is the use of a special workup procedure for the oxidation step. The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds.

SUBMITTER: Thongsornkleeb C

PROVIDER: S-EPMC2897060 | biostudies-literature | 2005 Mar

REPOSITORIES: biostudies-literature

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A practical method for the synthesis of 2-alkynylpropenals.

Thongsornkleeb Charnsak C Danheiser Rick L RL

The Journal of organic chemistry 20050301 6

A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation. Critical to the success of this approach is the use of a special workup procedure for the oxidation step. The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds. ...[more]

PMID: 15760233

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