Direct C3-functionalization of indoles with alpha-heteroaryl-substituted methyl alcohols via a metal-free hydrogen autotransfer-type reaction

05 July 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The Cs2CO3/oxone®-mediated C3-alkylation of indoles proceeds in moderate to high yields with a variety of C4–C7 functionalized indoles and is applicable to 2-, 3- and 4-hydroxymethyl pyridines and related electron-deficient heterocycles, permitting novel late-stage drug functionalizations and preparations of dimethyltryptamine analogs. Preliminary mechanistic studies support a chain process starting with an initital oxidation of the alcohol to the corresponding aldehyde, followed by a subsequent condensation onto indole and reduction/ hydride delivery from another equivalent of the primary alcohol.

Keywords

Hydrogen autotransfer
Indole heterocycles
Alcohols
Alkylation
Pyridine Heterocycles
Late-stage functionalization

Supplementary materials

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Title
Supplementary Information for: Direct C3-functionalization of indoles with alpha-heteroaryl-substituted methyl alcohols via a metal-free hydrogen autotransfer-type reaction
Description
Supplementary Tables and Experimental Part
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