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DOI: 10.1055/s-0028-1083587
Coupling of Cyclopropyl- and Cyclobutyl-trifluoroborates with Aryl Chlorides
Contributor(s):Paul Knochel, Andrei GavryushinUniversity of Pennsylvania, Philadelphia, USA
Cross-Coupling of Cyclopropyl- and Cyclobutyltrifluoroborates with Aryl and Heteroaryl Chlorides
J. Org. Chem. 2008, 73: 7481-7485
Publication History
Publication Date:
20 November 2008 (online)
Key words
cyclopropyl-trifluoroborates - aryl chlorides - arylcyclopropanes
Significance
Specific steric and electronic properties of cyclopropyl and cyclobutyl groups give interesting opportunities for the creation of new biologically active molecules. This convenient and versatile method protocol uses cycloalkyltrifluoroborates as shelf-stable cycloalkyl nucleophiles, and inexpensive aryl chlorides as coupling partners.
Comment
Cyclopropyl- and cyclobutylboronic acids are relatively unstable and difficult to store. The corresponding fluoroborates in these and many other cases are much more convenient. Interestingly, the preparation of cyclobutyl arenes by this cross-coupling reaction is significantly less smooth than their cyclopropyl analogues probably due to the decreased sp²-character of the cyclobutyl group.