Abstract
The recent progresses of the application of trifluoromethanesulfonyl chloride, CF3SO2Cl, in the formation of C–CF3, C–SCF3, C–SOCF3, and C–Cl bonds are summarised in this second part of a two-part review published back-to-back on both sodium trifluoromethanesulfinate, CF3SO2Na, (Part 1) and trifluoromethanesulfonyl chloride, CF3SO2Cl (Part 2). There are many reactions in common between these two reagents but it should be noted that CF3SO2Cl reacts under reductive conditions while CF3SO2Na requires oxidative conditions. Electrophilic chlorination is obviously the exclusive preserve of CF3SO2Cl that has been exploited with emphasis in enantioselective chlorination.
Highlights
We described the various uses of sodium trifluoromethanesulfinate in direct trifluoromethylation, trifluoromethylsulfenylation, trifluoromethylsufinylation and trifluoromethylsulfonylation reactions
We focused this second part of the review on the diverse uses of trifluoromethanesulfonyl chloride plus chlorination
In 2016, CF3SO2Cl was proposed for the first time as a new electrophilic trifluoromethylsulfenylation reagent by our research group [42]
Summary
We described the various uses of sodium trifluoromethanesulfinate in direct trifluoromethylation, trifluoromethylsulfenylation, trifluoromethylsufinylation and trifluoromethylsulfonylation reactions. We focused this second part of the review on the diverse uses of trifluoromethanesulfonyl chloride plus chlorination. The C-trifluoromethylsulfonylation is less reported than the corresponding O- and N-trifluoromethylsulfonylations, the resulting triflone group is an important synthetic tool for further functionalisation [4,5]. These sulfonylation reactions will not be further detailed hereafter. The direct introduction of CF3S and CF3S(O) motifs occupies a prime position in this review
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have