Issue 18, 2023

A phosphonium-based deep eutectic solvent promotes the stereoselective semi-reduction of internal alkynes to (Z)-alkenes

Abstract

Treatment of internal alkynes with Al powder, Pd/C and basic water in a methyltriphenylphosphonium bromide/ethylene glycol eutectic mixture resulted in highly chemoselective formation of (Z)-alkenes in a yield of up to 99% with Z/E stereoselectivity ranging from 63/37 to 99/1. The unusual catalytic activity of Pd/C is thought to be modulated by the in situ formation of a phosphine ligand.

Graphical abstract: A phosphonium-based deep eutectic solvent promotes the stereoselective semi-reduction of internal alkynes to (Z)-alkenes

Supplementary files

Article information

Article type
Communication
Submitted
20 Mar 2023
Accepted
13 Apr 2023
First published
14 Apr 2023

Org. Biomol. Chem., 2023,21, 3770-3777

A phosphonium-based deep eutectic solvent promotes the stereoselective semi-reduction of internal alkynes to (Z)-alkenes

A. N. Paparella, F. Messa, S. Perrone and A. Salomone, Org. Biomol. Chem., 2023, 21, 3770 DOI: 10.1039/D3OB00433C

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