Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Regioselective Photoisomerization/C−C Bond Formation of Asymmetric B(ppy)(Mes)(Ar): The Role of the Aryl Groups on Boron

Regioselective Photoisomerization/C−C Bond Formation of Asymmetric B(ppy)(Mes)(Ar): The Role of the Aryl Groups on Boron
Soren K. Mellerup, Cally Li, Tai Peng, Suning Wang
Asymmetric N,C-chelate organoboron compounds bearing two different aryl groups at the boron center undergo photoisomerization reactions that involve exclusively the less bulky aryl group, generating various strongly colored “dark isomers”. These species thermally isomerize to 4bH-azaborepin molecules by direct hydrogen atom transfer from a borirane cycle to the pyridyl moiety and ring expansion. Mechanistic insight into these highly regioselective transformations was obtained from kinetic data and through computational studies. Dark isomers: Asymmetric N,C-chelate boron compounds undergo a regioselective photoisomerization at the less bulky aryl group to intensely colored “dark isomers” and a subsequent thermal isomerization involving hydrogen atom transfer. This process demonstrates the definitive roles of steric and electronic effects in this photoresponsive system.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700096

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