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Tuning the Regioselective Functionalization of Trifluoromethylated Dienes via Lanthanum‐Mediated Single C−F Bond Activation.
- Source :
-
Chemistry - A European Journal . 2/24/2021, Vol. 27 Issue 12, p4016-4021. 6p. - Publication Year :
- 2021
-
Abstract
- 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/I2/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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *DIOLEFINS
*PERMUTATION groups
*LANTHANUM
*COUPLING reactions (Chemistry)
*ALDEHYDES
Subjects
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 27
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 148928393
- Full Text :
- https://doi.org/10.1002/chem.202005239