Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 12, Pages 4016-4021Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202005239
Keywords
C-C coupling; C-F activation; fulvene; lanthanides; mechanism
Categories
Funding
- French ANR [ANR-15-CE29-0020-01 ACTIV-CF-LAN]
- CNRS
- Universite de Reims Champagne-Ardenne
- Chinese Scholarship Council (CSC)
- Conseil Regional Champagne Ardenne
- Conseil General de la Marne
- Ministry of Higher Education and Research (MESR)
- EU-programme FEDER
Ask authors/readers for more resources
A highly selective method was developed in this study for the regio- and stereoselective addition of a variety of aldehydes onto trifluoromethylated benzofulvenes. The resulting products have potential for further applications and can be transformed into benzofulvenes carrying a difluorovinyl group.
The development of new fluorine-containing building blocks and their efficient synthetic access is currently a challenging research field. Herein, the highly regio- and stereoselective addition of a large range of aldehydes onto trifluoromethylated benzofulvenes was achieved using a simple La/I-2/DIBAL-Cl system via a selective C-F bond activation process. This versatile methodology provided homodienyl alcohols bearing a terminal CF2-alkene with potential further applications, as shown by the dehydration to the first benzofulvenes carrying a difluorovinyl group. In addition, for certain electron-poor aldehydes, unprecedented ipso substitution of the CF3 group in a diene was observed, which, according to DFT studies, is related to the presence of the large, Lewis-acidic lanthanum metal.
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