Direct catalytic trifluoromethylthiolation of boronic acids and alkynes employing electrophilic shelf-stable N-(trifluoromethylthio)phthalimide.
A new and safe method for the synthesis of N-(trifluoromethylthio)phthalimide, a convenient and shelf-stable reagent for the direct trifluoromethylthiolation, has been developed. N-(Trifluoromethylthio)phthalimide can be used as an electrophilic source of F3 CS(+) and reacts readily with boronic acids and alkynes under copper catalysis. The utility of CF3 S-containing molecules as biologically active agents, the mild reaction conditions employed, and the high tolerance of functional groups demonstrate the potential of this new methodology to be widely applied in organic synthesis as well as industrial pharmaceutical and agrochemical research and development.
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
Roman
R
Pluta
Pavlo
P
Nikolaienko
Magnus
M
Rueping
D000480:Alkynes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000480:Alkynes; D001897:Boronic Acids; D010797:Phthalimides; D013438:Sulfhydryl Compounds; C037431:phthalimide; D005461:Fluorine; D003300:Copper
alkynes; boron; copper; homogeneous catalysis; synthetic methods