Issue 19, 2023

Divergence in CH alkylation of indoles under Mn catalysis

Abstract

Achieving divergence in CH alkylation of substrates using feedstock chemicals is an attractive paradigm to enable the production of diverse products from the same starting materials. Herein, we report manganese-catalyzed CH alkylation of indole/indolines with alcohols, where product selectivity is achieved through catalyst control. By use of a molecularly defined PNP–Mn(I) complex, tandem double dehydrogenative CH alkylation of indoles is observed. In contrast, an NNN–Mn(II)-based catalyst system provides a diverse range of value-added bis(indolyl)methanes (BIMs) via an interrupted borrowing hydrogen strategy. The present strategy was successfully applied for sustainable, scalable synthesis of several life science molecules (vibrindole A, turbomycin B alkaloid, and antileukemic and anticancer agents) and natural products (gramine, dipterine, etc.).

Graphical abstract: Divergence in CH alkylation of indoles under Mn catalysis

Supplementary files

Article information

Article type
Paper
Submitted
27 Jul 2023
Accepted
16 Aug 2023
First published
24 Aug 2023
This article is Open Access
Creative Commons BY license

Catal. Sci. Technol., 2023,13, 5745-5756

Divergence in CH alkylation of indoles under Mn catalysis

A. Mondal, R. Kumar, A. K. Suresh, M. K. Sahoo and E. Balaraman, Catal. Sci. Technol., 2023, 13, 5745 DOI: 10.1039/D3CY01044A

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