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Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex
Author(s) -
Sandfort Frederik,
StriethKalthoff Felix,
Klauck Felix J. R.,
James Michael J.,
Glorius Frank
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804246
Subject(s) - borylation , chemistry , pyridinium , alkyl , photochemistry , combinatorial chemistry , molecule , acceptor , surface modification , electron acceptor , redox , radical , electron donor , catalysis , organic chemistry , physics , aryl , condensed matter physics
A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single‐electron reduction of redox‐active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light‐mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor–acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late‐stage functionalization of natural products and drug molecules.