Sulfonylation of Benzylic C−H Bonds through the Reaction of Aryl(o‐tolyl)methanones with Sulfonyl Hydrazides or Sulfonyl Chlorides

Abstract

A sulfonylation of benzylic C-H bonds of aryl(o-tolyl)methanones with arylsulfonyl hydrazides or arylsulfonyl chlorides has been developed. Arylsulfonyl hydrazides and arylsulfonyl chlorides were employed as sulfonylating reagents respectively to complete this transformation. During the reaction, enols were generated in situ from aryl(o-tolyl)methanones under UV irradiation, and subsequently reacted with sulfonyl radicals to provide a range of aryl(2-(arylsulfonylmethyl)aryl)methanones.

Transition‐Metal Free C(sp3)−H Sulfonylation for the Synthesis of 2‐Sulfolmethyl Quinolines from 2‐Methylquinolines and Sulfonyl Hydrazides

“…Based on the results of our controlled experiments and previous reports, [10,[56][57][58][59][60][61] a plausible mechanism is presented in Scheme 4. Firstly, tert-butoxyl and tert-butylperoxy radicals are formed through the decomposition of TBPB with iodine anion.…”

Facile Synthesis of Diatomite/β-Cyclodextrin Composite and Application for the Adsorption of Diphenolic Acid from Wastewater

“…The synthesis process of the DA/β-CD composite was shown in Figure 1. Firstly, the acylation happened between β-CD and p-toluenesulfonyl chloride [37], in which the hydrogen atom on the hydroxy group of β-CD was replaced by p-toluenesulfonyl chloride and produced Ts-β-CD. The pyridine was employed as a solvent and acid-binding agent during the reaction process, that not only accelerated the speed of the acylation reaction, but also prevented the formation of chlorinated alkanes.…”

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

“…A sulfonylation of benzylic CÀ H bonds of aryl (otolyl) methanones with arylsulfonyl chlorides was disclosed by Wu group. [101] Arylsulfonyl radical generated from homolysis of the arylsulfonyl chloride was proposed in the reaction mechanism. Enols were generated in situ from aryl (o-tolyl) methanones under UV irradiation, which could react with sulfonyl radicals to provide the desired product by further aromatization and oxidation reaction.…”

“…A sulfonylation of benzylic C−H bonds of aryl (otolyl) methanones with arylsulfonyl chlorides was disclosed by Wu group [101] . Arylsulfonyl radical generated from homolysis of the arylsulfonyl chloride was proposed in the reaction mechanism.…”