We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Selective Defluorination of Trifluoromethyl Substituents by Conformationally Induced Remote Substitution.
- Authors
Jesani, Mehul H.; Schwarz, Maria; Kim, Shiwhu; Evans, Finlay L.; White, Alexander; Browning, Alex; Abrams, Roman; Clayden, Jonathan
- Abstract
The selective reduction of an aromatic trifluoromethyl substituent to a difluoromethyl substituent may be achieved by base‐promoted elimination to form a difluoro‐p‐quinomethide which is trapped by an intramolecular nucleophile. High yields are obtained when the nucleophilic trap entails the conformationally favoured cyclisation of an aminoisobutyric acid (Aib) derivative. The resulting cyclised difluoromethyl‐substituted arylimidazolidinone products are readily converted to versatile difluoromethyl‐substituted aldehydes by reduction and hydrolysis. Defluorination is successful on a range of benzenoid (both para and ortho CF3‐substituted) and heterocyclic substrates. Double defluorination may likewise be achieved sequentially, or in a single step, from an Aib dipeptide derivative.
- Subjects
RING formation (Chemistry); HYDROLYSIS; ALDEHYDES; FLUORINE; ACIDS
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 24, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202403477