Organic Chemistry Portal



Catalytic Anti-Markovnikov Hydroallylation of Terminal and Functionalized Internal Alkynes: Synthesis of Skipped Dienes and Trisubstituted Alkenes

Melrose Mailig, Avijit Hazra, Megan K. Armstrong and Gojko Lalic*

*Department of Chemistry, University of Washington, Seattle, WA 98195, USA, Email:

M. Mailig, A. Hazra, M. K. Armstrong, G. Lalic, J. Am. Chem. Soc., 2017, 139, 6969-6977.

DOI: 10.1021/jacs.7b02104

see article for more reactions


The hydroallylation of terminal alkyl and aryl alkynes with simple allyl phosphates and 2-substituted allyl phosphates provides skipped dienes. The hydroallylation of functionalized internal alkynes enables the synthesis of complex trisubstituted alkenes.

see article for more examples

hydroallylation of an internal alkyne

Key Words

1,4-dienes, CuH, PMHS

ID: J48-Y2017