Catalytic Chemoselective and Stereoselective Semihydrogenation of Alkynes to E-Alkenes Using the Combination of Pd Catalyst and ZnI₂

Radhouan Maazaoui, Raoudha Abderrahim, Fabrice Chemla, Franck Ferreira, Alejandro Perez-Luna, Olivier Jackowski*

*Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire (IPCM), F-75252 Paris Cedex 05, France, Email: olivier.jackowskisorbonne-universite.fr

R. Maazaoui, R. Abderrahim, F. Chemla, F. Ferreira, A. Perez-Luna, O. Jackowski, Org. Lett., 2018, 20, 7544-7549.

DOI: 10.1021/acs.orglett.8b03295

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Abstract

The use of commercially available reagents (Cl₂Pd(PPh₃)₂, Zn⁰, and ZnI₂) enables an efficient E-selective semihydrogenation of internal alkynes under low dihydrogen pressure and low reaction temperature. The transformation involves syn-hydrogenation followed by isomerization.

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Key Words

semireduction of alkynes, hydrogen

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ID: J54-Y2018