Easy Access to SCF₂‐Containing Molecules through a Versatile Reagent

Abstract

A new fluoroalkylmethanesulfenamide reagent was developed to synthesize various molecules bearing the SCF2CO2Me group. Furthermore, the carboxyl function was successfully post‐transformed, through C–C coupling, for easy access to molecules containing the –SCF2– functionality.

Alkynylation of radicals: spotlight on the “Third Way” to transfer triple bonds

“…Almost simultaneously, Xu and Feng documented the same transformation without silver catalyst 40. The decarboxylative alkynylation of aryl- and thio-difluoroacetic acids was also successful 41…”

Trifluoromethylselenolation and Fluoroalkylselenolation of Alkenes by Electrophilic Addition

“…These two last functions open the way to various further post-functionalizations, as previously demonstrated. [15,16]…”

In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and (Z)-2-Alken-4-ynoates

“…In this regard, the development of new and efficient protocols for the synthesis of chalcogen-substituted isocoumarins or pyrones has received substantial attention during the last decades. − In 2011, Zeni’s group reported an FeCl 3 -mediated cyclization of alkynylaryl esters with different diorganyl dichalcogenides to afford 4-organochalcogenyl isochromenones in good yields (Scheme , method a). Furthermore, in 2014, Ding and co-workers reported incorporation of the CF 3 S– group into the isocoumarin scaffold through an electrophilic cyclization of o -(1-alkynyl)­benzoates with trifluoromethanesulfanylamide in the presence of BiCl 3 and BF 3 · Et 2 O (Scheme , method b).…”