Substituent-Controlled Regioselective Photoinduced Cyclization of N-Allylbenzamides with N-Sulfonylaminopyridinium Salts

Abstract

The annulation reactions of N-allylbenzamides with N-sulfonylaminopyridinium salts were developed under metal-free photoinduced mild conditions. Substituent-controlled sulfonaminoarylation and sulfonaminooxylation of benzamides were realized: N-allylbenzamides lead to benzosultams, while N-(2-phenylallyl)benzamides give sulfonamidylated oxazoline derivatives. Control experiments indicated that those reactions undergo a radical pathway with arylsulfonamidyl radicals as the intermediates. The aryl C−H bond functionalization in arylsulfonamidyl was involved for the first time to give benzosultams.

Electrochemical Trifluoromethylation and Sulfonylation of N-Allylamides: Synthesis of Oxazoline Derivatives

“…Commercial solvents and reagents were used without further purification unless otherwise noted. Substrates 1a – 1v and 1w were prepared according to the literature procedures.…”

Visible‐Light‐Driven Sulfonamidation of Arylazo Sulfonesthrough One‐Pot Multicomponent Reaction

“…[21][22][23] Photochemical reactions provide many useful organic synthetic processes. [24][25][26][27][28] Light energy can activate substrates and produce organic reactions under mild conditions. [27,29] Typically, photochemical methods are effectively used for reactions involving radical pathways to form CÀ C coupling or carbon-heteroatom bonds.…”

“…Photochemical reactions provide many useful organic synthetic processes [24–28] . Light energy can activate substrates and produce organic reactions under mild conditions [27,29] .…”

Silver-mediated radical cascade cyclization of N-allylamides with sodium sulfinates to access sulfonated oxazolines

“…4 However, their limitations are obvious, such as harsh reaction conditions and the utilization of excessive amounts of dehydrating agents. In recent years, electrophile- 5 or radical-induced 6 electrophilic cyclization of N -allylamides has emerged as a powerful tool for the synthesis of oxazoline derivatives. Among these, most reports focused on electrophilic cyclization of N -allylamides involving an ionic pathway, and radical-induced electrophilic cyclizations of N -allylamides are still limited and need further exploration.…”