Selective Monodefluorination and Wittig Functionalization of gem-Difluoromethyl Groups to Generate Monofluoroalkenes

• Published in: Journal of the American Chemical Society Vol. 140; no. 34; pp. 10682 - 10686
• Main Authors: Mandal, Dipendu, Gupta, Richa, Young, Rowan D
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 29.08.2018; Amer Chemical Soc
• Subjects: chemical reactions; Chemistry; Chemistry, Multidisciplinary; fluorides; Lewis acids; moieties; Physical Sciences; Science & Technology; ALKYL FLUORIDES; CONVERSION; POLYCYCLIC AROMATIC-HYDROCARBONS; TRIFLUOROMETHYLARENES; FRUSTRATED LEWIS PAIRS; ORGANOLITHIUM REAGENTS; CONCISE SYNTHESIS; ALPHA-FLUOROSTYRENE; F BOND ACTIVATION; HYDRODEFLUORINATION

Monodefluorination of gem-difluoromethyl groups is achieved using a frustrated Lewis pair (FLP) approach. Triarylphosphines and group 13 Lewis acids were surveyed as FLP components, with the combination of P­(o-Tol)3 and B­(C6F5)3 found to provide the best results, although the reaction is feasible...