Intramolecular Cyclizations of o-Substituted β,β-Difluorostyrenes: Synthesis of 3-Fluorinated Isochromenes and Isothiochromenes

Autor: Wada, Yukinori, Ichikawa, Junji, Katsume, Tadayuki, Nohiro, Tomoko, Okauchi, Tatsuo, Minami, Toru
Zdroj: Bulletin of the Chemical Society of Japan; May 2001, Vol. 74 Issue: 5 p971-977, 7p
Abstrakt: β,β-Difluorostyrenes bearing an oxygen (OH) or a sulfur (SH, SCOCH3) nucleophile linked by a methylene unit to the orthocarbon are prepared from 2,2,2-trifluoroethyl p-toluenesulfonate via the in situ generation of 2,2-difluorovinylboranes and their palladium-catalyzed cross-coupling reaction with aryl iodides. These styrene derivatives readily undergo intramolecular nucleophilic substitution of the oxygen and sulfur with loss of fluorine under basic conditions, leading to 3-fluoroisochromenes and 3-fluoroisothiochromenes in high yields.
Databáze: Supplemental Index