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Issue 79, 2019
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Switchable regioselection of C–H thiolation of indoles using different TMS counterions

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Abstract

A switchable regioselectivity in C–H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3–H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2–H thiolation of indoles was realized with the same set of substrates.

Graphical abstract: Switchable regioselection of C–H thiolation of indoles using different TMS counterions

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Article information


Submitted
22 Jul 2019
Accepted
09 Sep 2019
First published
09 Sep 2019

Chem. Commun., 2019,55, 11864-11867
Article type
Communication

Switchable regioselection of C–H thiolation of indoles using different TMS counterions

Y. Ji, H. Li, J. Zhang and Y. Wu, Chem. Commun., 2019, 55, 11864
DOI: 10.1039/C9CC05652A

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