A General N-alkylation Platform via Copper Metallaphotoredox and Silyl Radical Activation of Alkyl Halides.

ABSTRACT: The catalytic union of amides, sulfonamides, anilines, imines or N-heterocycles with a broad spectrum of electronically and sterically diverse alkyl bromides has been achieved via a visible light-induced metallaphotoredox platform. The use of a halogen abstraction-radical capture (HARC) mechanism allows for room temperature coupling of C(sp³ )-bromides using simple Cu(II) salts, effectively bypassing the prohibitively high barriers typically associated with thermally-induced S_N2 or S_N1 N-alkylation. This regio- and chemoselective protocol is compatible with >10 classes of medicinally-relevant N-nucleophiles, including established pharmaceutical agents, in addition to structurally diverse primary, secondary and tertiary alkyl brom

SUBMITTER: Dow NW 

PROVIDER: S-EPMC8372964 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature