Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 1, Pages 355-358Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508368
Keywords
Breslow intermediates; N-heterocyclic carbenes; radicals; rearrangement; thiamine
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Funding
- National Institute of General Medical Sciences of the National Institutes of Health (NIH) [P30 GM103450]
- Arkansas Biosciences Institute
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Breslow intermediates that bear radical-stabilizing N substituents, such as benzyl, cinnamyl, and diarylmethyl, undergo facile homolytic C-N bond scission under mild conditions to give products of formal [1,3] rearrangement rather than benzoin condensation. EPR experiments and computational analysis support a radical-based mechanism. Implications for thiamine-based enzymes are discussed.
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