Transition metal-free aroylation of NH-sulfoximines with methyl arenes

Abstract

A novel protocol towards N-aroylated sulfoximines from NH-sulfoximines and methyl arenes was herein demonstrated. The reaction took place in the presence of elemental iodine, requiring no external organic solvents, transition metal-catalysts or ligands. The aroylated products were obtained from the oxidative transformation in moderate to excellent yields (up to 94% yield) with a broad substrate scope (35 examples) through a radical pathway.

Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides

“…These sulfoximines have been deprotected to yield the free NH derivatives,a nd further functionalized to generate N-aryl, N-acyl, and N-alkyl, as well as cyclic derivatives,o ffering varying properties. [22] Thed irect synthesis of NH sulfoximines has largely involved undesirable reaction conditions,including harsh and explosive reagents. [23] Recently,ascalable synthesis of NH sulfoximines in continuous flow was reported by Kappe and co-workers using trimethylsilyl azide and fuming sulfuric acid to transfer an NH group directly to as ulfoxide intermediate of AZD6738, but racemization of the sulfur center occurred.…”

TBHP-mediated highly efficient dehydrogenative cross-oxidative coupling of methylarenes with acetanilides

“…According to the results of the control experiments, intermediate 6 also could be obtained from the reaction of benzaldehyde with 2a under the standard conditions. Then, intermediate 6 underwent a sequence of steps including fast oxidation and dehydration to give N -acetyl- N -phenylbenzamide ( 8 ) under the stipulated conditions , similar to the report of An [23]. Finally, the acidic hydrolysis of N -acetyl- N -phenylbenzamide ( 8 ) furnished the final product N -phenylbenzamide ( 3aa ).…”

Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions

“…15 Reports on the N-acylation with methylarene as acyl donors are also known (Scheme 1). [16][17][18][19] However, in such cases, pre-activation of the sulfoximines are essential for the transformation. For example, Bolm and his team reported the synthesis of N-acylated sulfoximines by treating Nchlorosulfoximines with methylarenes when using MnO 2 as the catalyst.…”