o-Quinone methide with overcrowded olefin component as a dehydridation catalyst under aerobic photoirradiation conditions.

ABSTRACT: An o-quinone methide (o-QM) featuring an overcrowded olefinic framework is introduced, which exhibits dehydridation activity owing to its enhanced zwitterionic character, particularly through photoexcitation. The characteristics of this o-QM enable the operation of dehydridative catalysis in the oxidation of benzylic secondary alcohols under aerobic photoirradiation conditions. An experimental analysis and density functional theory calculations provide mechanistic insights; the ground-state zwitterionic intermediate abstracts a hydride and proton simultaneously, and the active oxygen species facilitate catalyst regeneration.

SUBMITTER: Uraguchi D 

PROVIDER: S-EPMC8179400 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature