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Issue 40, 2020
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Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step

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Abstract

Efficient control of regioselectivity is a key concern in transition-metal-catalyzed direct C–H functionalization reactions. Various strategies for regiocontrol have been established by tuning the selectivity of the C–H activation step as a common mode. Herein, we present our study on an alternative mode of regiocontrol, in which the selectivity of the C–H activation step is no longer a key concern. We found that, in a reaction where the C–H activation step exhibits a different regio-preference from the subsequent functionalization step, a ligand-enabled switch of the regioselectivity-determining step could provide efficient regiocontrol. This mode has been exemplified by the Pd(II)-catalyzed aerobic oxidative Heck reaction of indoles, in which a ligand-controlled C3-/C2-selectivity was achieved for the first time by the development of sulfoxide-2-hydroxypyridine (SOHP) ligands.

Graphical abstract: Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step

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Supplementary files

Article information


Submitted
21 Apr 2020
Accepted
13 Sep 2020
First published
23 Sep 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 11042-11054
Article type
Edge Article

Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step

Y. Wang, C. Yuan, D. Chu and L. Jiao, Chem. Sci., 2020, 11, 11042
DOI: 10.1039/D0SC02246B

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