Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 30, Pages 9485-9490Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804515
Keywords
alkynes; carbenes; hydroboration; radical reactions; synthetic methods
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Funding
- JSPS KAKENHI [16K08159]
- US National Science Foundation
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Hydroboration of internal alkynes with N-heterocyclic carbene boranes (NHC-boranes) occurs to provide stable NHC (E)-alkenylboranes upon thermolysis in the presence of di-tert-butyl peroxide. The Eisomer results from an unusual trans-hydroboration, and the E/Z selectivity is typically high (90:10 or greater). Evidence suggests that this hydroboration occurs by a radical-chain reaction involving addition of an NHC-boryl radical to an alkyne to give a beta-NHC-borylalkenyl radical. Ensuing hydrogen abstraction from the starting NHC-borane provides the product and returns the starting NHC-boryl radical. Experiments suggest that the observed trans-selectivity results from kinetic control in the hydrogen-transfer reaction.
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