Copper(II)-Catalyzed Alkene Aminosulfonylation with Sodium Sulfinates For the Synthesis of Sulfonylated Pyrrolidones

Abstract

A copper-catalyzed direct aminosulfonylation of unactivated alkenes with sodium sulfinates for the efficient synthesis of sulfonylated pyrrolidones is described. This reaction features good functional group tolerance and wide substrate scope, providing an efficient and straightforward protocol to access this kind of pyrrolidones. Moreover, preliminary mechanistic investigations disclosed that a free-radical pathway might be invovled in the process.

Recent Advances in Silver‐Mediated Radical Difunctionalization of Alkenes

“… [11] The reaction tolerated a variety of functional groups regarding both of the functionalization partners under AgNO 3 /K 2 CO 3 catalytic system. A similar aminosulfonylation between alkene with sodium sulfinates was previously reported by Rao's group for the synthesis of sulfonylated pyrrolidones through the combination of Cu(OAc) 2 and Ag 2 CO 3 system [12] …”

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

“…Control experiments proved the radical nature of the developed process [231] . Using the Cu(OAc) 2 /Ag 2 CO 3 system in DMF at 100 °C, 5‐sulfonylmethyl γ‐lactams were obtained from aliphatic unsaturated amides and aromatic sodium sulfinates in 55–85% yields [232] . The reaction of 1,6‐enynes 419 with sulfonyl hydrazides 420 under oxidative conditions gave γ‐lactams 421 with (Z) / (E) ratio of 1:1 to 5:1.…”

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…Rao et al , reported a copper-catalyzed direct aminosulfonylation of unactivated alkenes with sodium sulfinates for the efficient synthesis of sulfonylated pyrrolidones via a 5- exo cyclization process ( Scheme 209 ). 316 Generally, the unsaturated quaternary amides reacted smoothly with sodium arylsulfinates and afforded the corresponding aminosulfonylation products in good to high yields. The reaction of α-substituted quaternary amides also generated the desired products in good yields with low diastereoselectivity ratios.…”