Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System.
A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of Csp2and Csp3nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.
Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Zhongyan
Z
Huang
Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Okiya
O
Matsubara
Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Shichong
S
Jia
Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Etsuko
E
Tokunaga
Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Norio
0000-0002-3742-4064
N
Shibata