Issue 18, 2021

An alternative mode to activate alcohols: application to the synthesis of N-heteroarene derivatives

Abstract

The activation of readily available but poorly reactive alcohols can be carried out solely in the presence of the tert-butoxide (KOtBu)/dimethylformamide (DMF) couple. This system allows the direct use of primary alcohols as alkylating agents to functionalize the C(sp3)–H bond of methyl azaarenes, in the absence of traditionally used transition metal-based catalysts. Various alkylated N-heteroarenes such as pyridine, quinoline, pyrazine or quinoxaline derivatives have been obtained by this method, which is supposed to proceed via the initial formation of an alkyl formate intermediate, as shown by experimental and theoretical mechanistic studies.

Graphical abstract: An alternative mode to activate alcohols: application to the synthesis of N-heteroarene derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
23 Jun 2021
Accepted
09 Jul 2021
First published
09 Jul 2021

Org. Chem. Front., 2021,8, 5112-5117

An alternative mode to activate alcohols: application to the synthesis of N-heteroarene derivatives

X. Liu, J. Sotiropoulos and M. Taillefer, Org. Chem. Front., 2021, 8, 5112 DOI: 10.1039/D1QO00930C

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