Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under ­experimental sonogashira conditions

Mikkel Andreas Christensen; Morten Rimmen Pedersen; Mogens Brøndsted Nielsen

doi:10.1055/s-0033-1339891

Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under experimental sonogashira conditions

Mikkel Andreas Christensen, Morten Rimmen Pedersen, Mogens Brøndsted Nielsen

Department of Chemistry

6 Citations (Scopus)

Abstract

The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented.

Original language	English
Journal	SYNLETT: Accounts and Rapid Communications in Chemical Synthesis
Volume	24
Issue number	20
Pages (from-to)	2715-2719
Number of pages	5
ISSN	0936-5214
DOIs	https://doi.org/10.1055/s-0033-1339891
Publication status	Published - 17 Dec 2013

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Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under experimental sonogashira conditions. / Christensen, Mikkel Andreas; Pedersen, Morten Rimmen; Nielsen, Mogens Brøndsted.

In: SYNLETT: Accounts and Rapid Communications in Chemical Synthesis, Vol. 24, No. 20, 17.12.2013, p. 2715-2719.

Research output: Contribution to journal › Journal article › Research › peer-review

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N2 - The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented.

AB - The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented.

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Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under ­experimental sonogashira conditions

Abstract

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Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under experimental sonogashira conditions