Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 14, Pages 5572-5576Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915500
Keywords
carbene transfer; C-H functionalization; fluorine; gem-difluoro olefins; palladium
Categories
Funding
- German Science Foundation
- Dean's Seed Fund of RWTH Aachen
- Boehringer Ingelheim Foundation
Ask authors/readers for more resources
A palladium catalyzed C-H functionalization and consecutive beta-fluoride elimination reaction between indole heterocycles and fluorinated diazoalkanes is reported. This approach provides for the first time a facile method for the rapid synthesis of gem-difluoro olefins using fluorinated diazoalkanes under mild reaction conditions. Cyclopropanation products were obtained when N-arylated rather than N-alkylated indoles were applied in this reaction. Mechanistic studies reveal the importance of the beta-fluoride elimination step in this transformation. This method presents a new concept for the simple and direct transfer of a 1-aryl-(2,2-difluorovinyl) group to access gem-difluoro olefins.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available