Electrosynthesis using a fluoride ion mediator. IV: Fluoride ion mediated anodic alpha-methoxylation of 2-methoxy-3,3,3-trifluoropropyl phenyl sulfide and its synthetic application

摘要

Anodic,oxidation of 2-methoxy-3,3,3-trifluoropropyl phenyl sulfide was carried out in methanol containing Et3N . 3HF to provide the corresponding alpha-methoxylated product in good yield. Nucleophilic substitution of the alpha-methoxylated product with carbon nucleophiles such as arenes and allylsilane was successfully carried out in the presence of TiCl4 and the carbon nucleophiles were introduced into the beta-position to the CF3 group in moderate yields and with high or reasonable diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 12]