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Direct Activation of a Remote C(sp 3 )–H Bond Enabled by a Visible‐Light Photosensitized Allene Moiety
Author(s) -
Liu Jiaxin,
Wei Yin,
Shi Min
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202101266
Subject(s) - allene , chemistry , moiety , photochemistry , excited state , reactivity (psychology) , derivative (finance) , hydrogen atom abstraction , hydrogen atom , deuterium , substrate (aquarium) , radical , stereochemistry , catalysis , organic chemistry , group (periodic table) , pathology , medicine , physics , alternative medicine , oceanography , geology , nuclear physics , financial economics , economics , quantum mechanics
Despite allene derivatives have been always regarded as a radical accepter in traditional radical chemistry for decades, the reactivity of allene derivatives under excited state in radical chemistry was rarely explored. Herein, we wish to report an example to engage triplet‐excited state of allene moiety as hydrogen‐atom‐transfer (HAT) partner in the activation of remote sp 3 C−H bond via visible‐light irradiation under mild reaction conditions with broad substrate scope and good functional‐group tolerance. The reaction mechanism involving the generation of triplet excited state of allene derivative and the subsequent HAT process was supported by deuterium labeling, kinetic analysis experiments and DFT calculations.