Back to Search
Start Over
Phosphine-catalyzed regio- and stereo-selective hydroboration of ynamides to (Z)-β-borylenamides.
- Source :
-
Chemical Communications . 12/25/2022, Vol. 58 Issue 99, p13751-13754. 4p. - Publication Year :
- 2022
-
Abstract
- We report a tri-n-butyl phosphine catalyzed regio- and stereo-selective hydroboration of ynamides to yield (Z)-β-borylenamides in good yields. Surprisingly, a formal cis addition to the triple bond was observed as confirmed by NMR and X-ray crystallography. 31P NMR studies suggest that a zwitterionic vinylphosphonium intermediate is key in the mechanism. The resulting products were further transformed to β-CF3 enamides via stereoretentive trifluoromethylation. [ABSTRACT FROM AUTHOR]
- Subjects :
- *YNAMIDES
*HYDROBORATION
*X-ray crystallography
*PHOSPHINES
Subjects
Details
- Language :
- English
- ISSN :
- 13597345
- Volume :
- 58
- Issue :
- 99
- Database :
- Academic Search Index
- Journal :
- Chemical Communications
- Publication Type :
- Academic Journal
- Accession number :
- 160754801
- Full Text :
- https://doi.org/10.1039/d2cc04543e