Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 22, Pages 6093-6097Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700096
Keywords
4bH-azaborepins; boriranes; C-C bond formation; photo-/thermal transformations; regioselectivity
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Funding
- Natural Science and Engineering Research Council of Canada [RGPIN1193993-2013]
- National Natural Science Foundation of China [21571017]
- Canadian Government
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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.
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