67736-18-9Relevant articles and documents
Acid-mediated intermolecular C-F/C-H cross-coupling of 2-fluorobenzofurans with arenes: Synthesis of 2-arylbenzofurans
Fujita, Takeshi,Morioka, Ryutaro,Fukuda, Takuya,Suzuki, Naoto,Ichikawa, Junji
supporting information, p. 8500 - 8503 (2021/08/31)
Transition-metal-free acid-promoted biaryl construction was achieved via intermolecular C-F/C-H cross-coupling. By treating 2-fluorobenzofurans with arenes in the presence of AlCl3, 2-arylbenzofurans were obtained. This protocol was successfully applied to the short-step orthogonal synthesis of a bioactive 2-arylbenzofuran natural product, which allows independent transformations of C-F and C-Br bonds. Mechanistic studies indicated that α-fluorine-stabilized carbocations, generated via the protonation of 2-fluorobenzofurans, served as key intermediates. The Friedel-Crafts-type C-C bond formation between the α-fluorocarbocations and arenes, followed by hydrogen fluoride elimination, afforded 2-arylbenzofurans. This journal is