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Synthesis 2010(15): 2621-2625  
DOI: 10.1055/s-0029-1218848
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Tandem Suzuki-Miyaura Cross-Coupling/Dehydrobromination of 1,1-Dibromoalkenes to Alkynes with a Cyclobutene-1,2-diylbis(imidazolium) Salt as Catalyst Precursor

Alireza Rahimi, Andreas Schmidt*
Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany
Fax: +49(5323)723861; e-Mail: schmidt@ioc.tu-clausthal.de;
Further Information

Publication History

Received 17 February 2010
Publication Date:
25 June 2010 (online)

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Abstract

A cyclobutene-1,2-bis(imidazolium) salt proved to be an efficient catalyst precursor for one-pot tandem Suzuki-Miyaura/dehydrobromination­ reactions for the synthesis of alkynes starting from 1,1-dibromoalkenes and palladium(II) acetate, aryl boronic acids, and potassium tert-butoxide in toluene. Starting materials were prepared from aldehydes under Corey-Fuchs conditions.

Key words

imidazol-2-ylidene - N-heterocyclic carbene - biscarbene complex - Corey-Fuchs reaction

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