Open AccessPhotocatalytic Generation of Aminium Radical Cations for C–N Bond Formation
Author(s) -
Jacob M. Ganley,
Philip R. D. Murray,
Robert R. Knowles
Publication year - 2020
Publication title -
acs catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.898
H-Index - 198
ISSN - 2155-5435
DOI - 10.1021/acscatal.0c03567
Subject(s) - hydroamination , chemistry , amination , photocatalysis , photoredox catalysis , alkene , electrophile , photochemistry , bond cleavage , catalysis , context (archaeology) , radical ion , combinatorial chemistry , organic chemistry , ion , paleontology , biology
Aminium radical cations have been extensively studied as electrophilic aminating species that readily participate in C─N bond forming processes with alkenes and arenes. However, their utility in synthesis has been limited, as their generation required unstable, reactive starting materials and harsh reaction conditions. Visible-light photoredox catalysis has emerged as a platform for the mild production of aminium radical cations from either unfunctionalized or N -functionalized amines. This Perspective covers recent synthetic methods that rely on the photocatalytic generation of aminium radical cations for C─N bond formation, specifically in the context of alkene hydroamination, arene C─H bond amination, and the mesolytic bond cleavage of alkoxyamines.