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Nickel-catalyzed cross-coupling reactions of bicyclo[1.1.0]butylmagnesium bromide and bicyclo[1.1.0]butyllithium derivatives with alkynyl chlorides and bromides

✍ Scribed by Stephen, A. ;Hashmi, K. ;Vollmer, Antje ;Szeimies, Günter

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
535 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Several alkynylbicyclo[1.1.0]butanes are prepared by coupling of bicyclo[1.1.0]butylmagnesium bromide with alkynyl chlorides. Severe side reactions, which take place with alkynyl bromides, are not observed. Bridgehead‐lithiated bicyclo[1.1.0]butanes are also effective components in these reactions. The coupling occurs by nickel catalysis as shown by control experiments, an uncatalyzed nucleophilic substitution at the acetylenic carbon atom not being a major reaction path. Alkyl‐ and aryllithium compounds could also be coupled with alkynyl chloride 13c, but in the case of alkynyllithium reagents side reactions decreased the synthetic value of this alkynylic coupling procedure.

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