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Palladium-Catalyzed Alkyne Insertion/Reduction Route to Trisubstituted Olefins

Erin R. Fruchey, Brendan M. Monks, Andrea M. Patterson and Silas P. Cook*

*Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States, Email: sicookindiana.edu

E. R. Fruchey, B. M. Monks, A. M. Patterson, S. P. Cook, Org. Lett., 2013, 15, 4362-4365.

DOI: 10.1021/ol4018694 (free Supporting Information)


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Abstract

A route to trisubstituted olefins through a palladium-catalyzed alkyne insertion with unactivated alkyl iodides followed by a reduction proceeds under mild conditions and tolerates a range of functional groups and substitution patterns. Mechanistic inquiry suggests that the transformation proceeds through a hybrid radical/organometallic pathway.

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Key Words

cyclopentanes, phenylsilane


ID: J54-Y2013