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Issue 71, 2019
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Rhodium(i)-catalyzed mono-selective C–H alkylation of benzenesulfonamides with terminal alkenes

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Abstract

The Rh(I)-catalyzed ortho-alkylation of benzenesulfonamides with alkenes with the aid of an 8-aminoquinoline directing group is reported. The reaction is applicable to a variety of benzenesulfonamide derivatives and various alkenes. Curiously, unactivated 1-alkenes were more reactive than activated alkenes. Deuterium labeling experiments indicate that an unusual 1,2-H shift mechanism to generate a carbene rhodium intermediate is involved.

Graphical abstract: Rhodium(i)-catalyzed mono-selective C–H alkylation of benzenesulfonamides with terminal alkenes

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Supplementary files

Article information


Submitted
08 Jul 2019
Accepted
05 Aug 2019
First published
05 Aug 2019

Chem. Commun., 2019,55, 10503-10506
Article type
Communication

Rhodium(I)-catalyzed mono-selective C–H alkylation of benzenesulfonamides with terminal alkenes

S. Rej and N. Chatani, Chem. Commun., 2019, 55, 10503
DOI: 10.1039/C9CC05219D

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