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Regioselective Radical Hydroboration of gem -Difluoroalkenes: Synthesis of α-Borylated Organofluorines.
- Source :
-
Organic letters [Org Lett] 2019 Oct 18; Vol. 21 (20), pp. 8414-8418. Date of Electronic Publication: 2019 Oct 09. - Publication Year :
- 2019
-
Abstract
- A regioselective radical hydroboration of gem -difluoroalkenes was developed for the synthesis of α-difluoroalkylborons. The reaction features excellent regioselectivity, broad substrate scope, and good functional group capability. DFT calculations implicated the remarkable α-selectivity was driven from the kinetically and thermodynamically more favorable α-addition step. The resulting α-difluoroalkylborons could be readily converted into NHC-borane-tethered monofluoroalkenes, which demonstrated unique reactivity and applicability in the synthesis of monofluoroalkene derivatives through transformations of the boron unit.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 21
- Issue :
- 20
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 31596598
- Full Text :
- https://doi.org/10.1021/acs.orglett.9b03173