Copper(I)-Catalyzed Allylic Substitutions with a Hydride Nucleophile

T. N. Thanh Nguyen, Niklas O. Thiel, Felix Pape and Johannes F. Teichert*

*Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 115, 10623 Berlin, Germany, Email: johannes.teichertchem.tu-berlin.de

T. N. T. Nguyen, N. O. Thiel, F. Pape, J. F. Teichert, Org. Lett., 2016, 18, 2455-2458.

DOI: 10.1021/acs.orglett.6b00941

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Abstract

An easily accessible copper(I)/N-heterocyclic carbene (NHC) complex enables a regioselective allylic reduction of allylic bromides with (TMSO)₂Si(Me)H as hydride source. The reaction provides aryl- and alkyl-substituted branched α-olefins in good yields, which are valuable building blocks for synthesis.

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Key Words

dehalogenations, olefins, silanes

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ID: J54-Y2016