A Practical Preparation of Terminal Alkynes from Aldehydes

Zhe Wang*, Silvio Campagna, Kaihong Yang, Guoyou Xu, Michael E. Pierce, Joseph. M. Fortunak and Pat. N. Confalone

*DuPont Pharmaceuticals Company, Research & Development, Chambers Works, Deepwater, New Jersey 08023

Z. Wang, S. Campagna, K. Yang, G. Xu, M. E. Pierce, J. M. Fortunak, P. N. Confalone, J. Org. Chem., 2000, 65, 1889-1891.

DOI: 10.1021/jo9916582

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Abstract

An efficient, practical, and economical procedure for the conversion of aldehydes into terminal alkynes contains of three steps: addition of trichloromethyl anion generated in situ from trichloroacetic acid to aldehydes; sulfonylation; and finally, sequential elimination of chloride, tosylate, and HCl followed by metalation of the remaining chloride and protonation to generate the desired alkynes.

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reaction pathway / proposed mechanism

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Key Words

terminal alkynes, Corey-Fuchs reaction

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ID: J42-Y2000