Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 40, Pages 21697-21701Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107647
Keywords
1; 2-carboboration; catalyst-free reaction; synthetic methods; trisubstituted alkenylboronates; ynamides
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Funding
- Deutsche Forschungsgemeinschaft DFG [IRTG 2678]
- European Research Council (ERC) [692640]
- KAKENHI from the Japan Society for the Promotion of Science (JSPS) [18H05261]
- JSPS
- MEXT (WISE Program)
- Projekt DEAL
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The study introduces a catalyst-free 1,2-carboboration reaction of ynamides, which shows high yields with complete regio- and stereoselectivity, yielding valuable enamide compounds with synthetic potential.
Catalyst-free 1,2-carboboration of ynamides is presented. Readily available aryldichloroboranes react with alkyl- or aryl-substituted ynamides in high yields with complete regio- and stereoselectivity to valuable beta-boryl-beta-alkyl/aryl alpha-aryl substituted enamides which belong to the class of trisubstituted alkenylboronates. The 1,2-carboboration reaction is experimentally easy to conduct, shows high functional group tolerance and broad substrate scope. Gram-scale reactions and diverse synthetic transformations convincingly demonstrate the synthetic potential of this method. The reaction can also be used to access 1-boraphenalenes, a class of boron-doped polycyclic aromatic hydrocarbons.
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