A Germanium Catalyst Accelerates the Photoredox α-C(sp3)-H Alkylation of Primary Amines

Kentaro Sakai; Kounosuke Oisaki; Motomu Kanai

doi:10.1021/acs.orglett.2c00871

A Germanium Catalyst Accelerates the Photoredox α-C(sp³)-H Alkylation of Primary Amines

Org Lett. 2022 May 13;24(18):3325-3330. doi: 10.1021/acs.orglett.2c00871. Epub 2022 Apr 29.

Authors

Kentaro Sakai¹, Kounosuke Oisaki¹, Motomu Kanai¹

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.

PMID: 35486160
DOI: 10.1021/acs.orglett.2c00871

Abstract

Site-selective C(sp³)-H functionalizations using photoredox catalysis (PC) and hydrogen atom transfer (HAT) catalysis have received increasing attention. Here, we report a Ph₂GeCl₂ cocatalyst that greatly improves the yield of α-C(sp³)-H alkylation of primary amines catalyzed by a PC-HAT hybrid system. The α-position of the amino group selectively reacted even when weaker C-H bonds existed in the substrates. This finding may help the design of a novel site-selective hybrid catalysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Amines* / chemistry
Carbon / chemistry
Catalysis
Germanium*
Hydrogen / chemistry
Oxidation-Reduction

Substances

Amines
Germanium
Carbon
Hydrogen