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Catalyst‐Free Deaminative Functionalizations of Primary Amines by Photoinduced Single‐Electron Transfer
Author(s) -
Wu Jingjing,
Grant Phillip S.,
Li Xiabing,
Noble Adam,
Aggarwal Varinder K.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814452
Subject(s) - chemistry , pyridinium , primary (astronomy) , catalysis , alkyl , photoinduced electron transfer , alkylation , reactivity (psychology) , functional group , electron transfer , photochemistry , photocatalysis , organic chemistry , radical , combinatorial chemistry , medicine , physics , alternative medicine , polymer , pathology , astronomy
The use of pyridinium‐activated primary amines as photoactive functional groups for deaminative generation of alkyl radicals under catalyst‐free conditions is described. By taking advantage of the visible light absorptivity of electron donor–acceptor complexes between Katritzky pyridinium salts and either Hantzsch ester or Et 3 N, photoinduced single‐electron transfer could be initiated in the absence of a photocatalyst. This general reactivity platform has been applied to deaminative alkylation (Giese), allylation, vinylation, alkynylation, thioetherification, and hydrodeamination reactions. The mild conditions are amenable to a diverse range of primary and secondary alkyl pyridiniums and demonstrate broad functional group tolerance.