Nickel-catalyzed oxidative coupling reactions of two different terminal alkynes using O(2) as the oxidant at room temperature: facile syntheses of unsymmetric 1,3-diynes

Weiyan Yin; Chuan He; Mao Chen; Heng Zhang; Aiwen Lei

doi:10.1021/ol8027863

Nickel-catalyzed oxidative coupling reactions of two different terminal alkynes using O(2) as the oxidant at room temperature: facile syntheses of unsymmetric 1,3-diynes

Org Lett. 2009 Feb 5;11(3):709-12. doi: 10.1021/ol8027863.

Authors

Weiyan Yin¹, Chuan He, Mao Chen, Heng Zhang, Aiwen Lei

Affiliation

¹ College of Chemistry and Molecular Sciences, Wuhan University, PR China.

PMID: 19108674
DOI: 10.1021/ol8027863

Abstract

Two different terminal alkynes now can be coupled together in the presence of NiCl(2).6H(2)O/CuI by using an excess of one of the terminal alkyne substrates. The new method employed 20 mol % TMEDA as the ligand and environmentally benign O(2) or air as the oxidant. It is the first example using Ni-salt as catalyst by employing air or O(2) as oxidant, which led to efficient heterocoupling of two different alkynes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Copper / chemistry
Diynes / chemical synthesis*
Diynes / chemistry
Molecular Structure
Nickel / chemistry*
Oxidation-Reduction

Substances

Alkynes
Diynes
Copper
Nickel