Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 18, Pages 5498-5501Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201500487
Keywords
1,1-hydroboration; BN heterocycles; boryl insertion; thermal elimination
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Funding
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- NSERC
- Canada Council for the Art
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Boranes with the general formula of HBR2 have been found to undergo a facile 1,1-hydroboration reaction with pyrido[1,2-a]isoindole (A), resulting in insertion of a BR2 unit into a C-N bond and the formation of a variety of BN heterocycles. Investigation on the thermal reactivity of the BN heterocycles revealed that these molecules have two distinct and competitive thermal elimination pathways: HBR2 elimination (or retro-hydroboration) versus R-H elimination, depending on the R group on the B atom and the chelate backbone. Mechanistic aspects of these highly unusual reactions have been established from both experimental and computational evidence. Adduct formation between HBR2 and A was found to be the key intermediate in 1,1-hydroboration of A.
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