This paper describes that an amide-base generated in situ from tetramethylammonium fluoride (TMAF) and N(TMS) 3 catalyzes the deprotonative coupling of benzylic C(sp 3 )-H bonds with carbonyls to form stilbenes. A variety of methylheteroarenes (2-methylbenzothiophene, 2-methylbenzofuran, and 2-, 3-, or 4-methylpyridines) are used as nucleophiles. Application to enamine synthesis using DMF as an electrophile is also shown. The present system is effective for toluenes (4-phenyl-, 4-bromo-, 2-bromo-, and 4-chlorotoluenes) having low reactivity.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry