Issue 71, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
08 Jul 2019
Accepted
05 Aug 2019
First published
05 Aug 2019

Chem. Commun., 2019,55, 10503-10506

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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