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Catalytic Hydrodefluorination of C−F Bonds by an Air‐Stable P III Lewis Acid
Author(s) -
Chitnis Saurabh S.,
Krischer Felix,
Stephan Douglas W.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801305
Subject(s) - chemistry , catalysis , lewis acids and bases , reagent , aryl , medicinal chemistry , organic chemistry , alkyl
Catalytic hydrodefluorination (HDF) of unactivated fluoroalkanes or CF 3 ‐substituted aryl species is performed using the P III Lewis acids, [(bipy)PPh] 2+ ( 1 2+ ) and [(terpy)PPh] 2+ ( 2 2+ ) under mild conditions (25 or 50 °C). Mechanistic studies indicate that activation of C−F bond by the P III center is key. Particularly noteworthy is that the catalyst 2 [B(C 6 F 5 ) 4 ] 2 is air‐stable and readily accessible from bench‐stable, commercially available reagents in one‐step and can be used without isolation.