Tunable photocatalytic oxysulfonylation and chlorosulfonylation of α-CF₃ alkenes with sulfonyl chlorides

Abstract

Tunable photoredox-catalyzed chlorosulfonylation and oxysulfonylation of α-trifluoromethylstyrenes with sulfonyl chloride were facilely achieved by simply manipulating photocatalyst and solvent. This strategy makes full use of the structural features of sulfonyl...

Efficient access to β-amino acid ester/β-amino ketone derivatives via photocatalytic radical alkoxycabonylimidation/carbonylimidation of alkenes

“…Currently, a limited number of examples have been modified by radical ionic bifunctionalization. 18 In 2021, Han and co-workers reported the synthesis of CF 3 -substituted β-amino ketones by the radical method. 19 Hence, radical difunctionalization involving the bifunctional reagent 2a reported here via a radical–radical cross-coupling process was explored.…”

Fe-catalyzed hydroxytrifluoromethylation of α-(trifluoromethyl)styrenes with CF3SO2Na: facile access to α,β-bistrifluoromethyl tertiary alcohols

“…Remarkably, hydroxyletherification and hydroxylsulfonylation of α-(trifluoromethyl)styrenes with various substrates under different reaction conditions could afford a variety of α-trifluoromethyl β-heteroatom substituted tertiary alcohols and α-trifluoromethyl-β-sulfonyl tertiary alcohols, respectively (Scheme 4a–e). 12 In continuation of our interest in addition reaction of α-(trifluoromethyl)styrenes, 13 in this paper, we disclosed a simple and efficient method for the synthesis of α,β-bistrifluoromethyl tertiary alcohols via Fe-catalyzed hydroxytrifluoromethylation of α-(trifluoromethyl)styrenes with CF 3 SO 2 Na in the presence of K 2 S 2 O 8 and air (Scheme 4f).…”

Divergent Synthesis of Organofluorinated Molecules from Titanium Mediated Deoxygenation of Free Alcohols

“…[ 12‐21 ] By contrast, the hydroalkylation of α‐trifluoromethylstyrenes via radical addition with the retention of three C—F bonds remains largely unexplored. [ 22‐28 ] Recently, Shen and coworkers developed an elegant strategy for the preparation of both gem ‐difluoroalkenes and trifluoromethyl alkanes with α‐CF 3 ‐olefins and α‐silyl alcohols via reductive quenching‐initiated photoredox conditions. [ 24 ] The employment of two catalysts that possess different reduction potentials is the key to control the reactivity of α‐CF 3 carbon radicals to be further reduced to carbanions or undergo hydrogen atom transfer process (Figure 1b).…”