Open AccessAccessing Aliphatic Amines in C–C Cross-Couplings by Visible Light/Nickel Dual Catalysis
Author(s) -
Weizhe Dong,
Shorouk O. Badir,
Xuange Zhang,
Gary A. Molander
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c01207
Subject(s) - chemistry , catalysis , nickel , visible spectrum , dual (grammatical number) , photochemistry , combinatorial chemistry , organic chemistry , optoelectronics , art , physics , literature
A general aminoalkylation of aryl halides was developed, overcoming intolerance of free amines in nickel-mediated C-C coupling. This transformation features broad functional group tolerance and high efficiency. Taking advantage of the fast desilylation of α-silylamines upon single-electron transfer (SET) facilitated by carbonate, α-amino radicals are generated regioselectively, which then engage in nickel-mediated C-C coupling. The reaction displays high chemoselectivity for C-C over C-N bond formation. Highly functionalized pharmacophores and peptides are also amenable.