Design and synthetic utility of new HAT organocatalysts derived from commercially available diamines

Abstract

A series of hydrogen-atom transfer (HAT) organocatalysts were conveniently prepared from commercially available diamine compounds, and their utility in photoinduced HAT catalysis ability was investigated. The combination of these readily available HAT organocatalysts with the Fukuzumi photoredox catalyst enables efficient and site-selective C–H alkylation of various functionalized substrates ranging from simple hydrocarbons to complex molecules. Notably, the sequential one-pot photoinduced dialkylations of bifunctional substrates can be realized. Mechanistic studies suggested that the 1-naphthylmethyl moiety on one nitrogen atom of the diamine compounds plays a crucial role in the reaction by inducing the facile generation of a cationic aminium radical on the other nitrogen of the diamine as an active intermediate for the HAT process.

Graphical abstract: Design and synthetic utility of new HAT organocatalysts derived from commercially available diamines

Supplementary files

Article information

Article type
Research Article
Submitted
15 Mar 2025
Accepted
02 May 2025
First published
06 May 2025
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2025, Advance Article

Design and synthetic utility of new HAT organocatalysts derived from commercially available diamines

J. Jia, T. Kato and K. Maruoka, Org. Chem. Front., 2025, Advance Article , DOI: 10.1039/D5QO00509D

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