Issue 2, 2009

Homocoupling reaction of terminal alkynes catalyzed by a reusable cationic 2,2′-bipyridyl palladium(II)/CuI system in water

Abstract

A cationic 2,2′-bipyridyl palladium(II)/CuI system was proven to be a reusable and highly efficient catalyst for the homocoupling of terminal alkynes at room temperature using water as a solvent in the presence of TBAB under aerobic conditions. For aromatic terminal alkynes, the reaction was performed either with or without I2 as an oxidant; the addition of I2 was required when aliphatic terminal alkynes were used as a substrate for the homocoupling reaction. In the presence of 0.0001–1 mol% palladium catalyst and 1 mol% CuI, a variety of terminal alkynes were homocoupled in good to excellent yields. The water-soluble catalytic system was separated from the organic products by extraction and the residual aqueous solution showed activity for reuse for several cycles without a significant decrease in activity.

Graphical abstract: Homocoupling reaction of terminal alkynes catalyzed by a reusable cationic 2,2′-bipyridyl palladium(II)/CuI system in water

Supplementary files

Article information

Article type
Paper
Submitted
25 Sep 2008
Accepted
13 Nov 2008
First published
05 Dec 2008

Green Chem., 2009,11, 269-274

Homocoupling reaction of terminal alkynes catalyzed by a reusable cationic 2,2′-bipyridyl palladium(II)/CuI system in water

S. Chen, W. Wu and F. Tsai, Green Chem., 2009, 11, 269 DOI: 10.1039/B815812F

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