The Copper‐Catalyzed Oxidative N‐Acylation of Sulfoximines

Abstract

An oxidative cross-coupling reaction between aldehydes and sulfoximines involving dual C À H/N À H functionalization has been developed. This reaction process is facilitated by a simple copper catalyst (1 mol% loading) and tert-butyl hydroperoxide (TBHP) as the oxidant and proceeds under mild reaction conditions to afford a series of valuable N-acylated sulfoximine derivatives in excellent yields.

Rhodium(III)‐Catalyzed Selective ortho‐Olefinations of N‐Acyl and N‐Aroyl Sulfoximines by CH Bond Activation

“…In using N ‐aroyl‐protected derivatives we envisaged additional opportunities 12. For this purpose, S,S ‐dimethyl sulfoximine was converted into α,β‐unsaturated carbonyl compounds 5 a – e by using standard protocols 13. Under similar reaction conditions as previously, aroyl‐substituted sulfoximines 5 a and 5 b reacted well with 2 a , affording alkenylated products 6 a and 6 b in yields of 92 and 73 %, respectively (Scheme ).…”

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

“…Nevertheless, the mechanism of the newly developed aroylation protocol remained blurry. According to the report from Bolm [10] , it was considered the reaction might take place via the acyl-radical intermediate. Therefore, control reactions were conducted for clarification ( Figure 1).…”

“…For example, Bolm has disclosed a copper(I)-catalyzed N-aroylation method from NH-sulfoximines and benzaldehydes under the oxidative conditions through a dual C-H/N-H activations pathway. [10] Then, another aroylation protocol of N-chloro sulfoximines with methyl arenes was described from the same group, using MnO 2 as the catalyst. [11] Meanwhile, it is noteworthy that methyl arenes have been applied successfully for the formation of carbon-heteroatom bonds through the C-H activation and successive oxidative functionalization pathway.…”

Copper-catalyzed preparation of N-aroylated sulfoximines from methylarenes

“…Recently, benzaldehydes were successfully employed as the aroylation reagent for the coupling with NH-sulfoximines in the presence of Cu(I). [10] The coupling methodology developed by Bolm and coworkers proceeded through a dual C-H/N-H activations pathway under the oxidative conditions. Then, readily-accessible methylarenes were also successfully applied for the aroylation of N-chloro sulfoximines under MnO 2 -mediated system by the same research group.…”