Ni-Catalyzed Reductive Liebeskind–Srogl Alkylation of Heterocycles

Ma, Yuanhong; Cammarata, Jose; Cornella, Josep

doi:10.1021/jacs.8b13534

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Ni-Catalyzed Reductive Liebeskind–Srogl Alkylation of Heterocycles

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Ma, Yuanhong
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cammarata, Jose
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cornella, Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Ma, Y., Cammarata, J., & Cornella, J. (2019). Ni-Catalyzed Reductive Liebeskind–Srogl Alkylation of Heterocycles. Journal of the American Chemical Society, 141(5), 1918-1922. doi:10.1021/jacs.8b13534.

Cite as: https://hdl.handle.net/21.11116/0000-0003-3D99-D

Abstract

Herein we present a Ni-catalyzed alkylation of C–SMe with alkyl bromides for the decoration of heterocyclic frameworks. The protocol, reminiscent to the Liebeskind–Srogl coupling, makes use of simple C(sp2)–SMe to be engaged in a reductive coupling. The reaction is suitable for a preponderance of highly valuable heterocyclic motifs. In addition to cyclic bromides, noncyclic alkyl bromides are well accommodated with exquisite levels of retention over isomerization. The protocol is scalable and permits orthogonal couplings in the presence of other functionalization handles.