Cp∗Rh/Ag catalyzed C–H activation/cyclization sequences of NH-sulfoximines to fused aza-polyheterocycles under gentle conditions

• DOI: 10.1016/j.gresc.2022.06.002
• Publication Date: 2022-06-18T06:05:39Z
• Authors: Jiapian Huang; Fei Liu; Feihua Du; Linghui Zeng; Zhiyuan Chen
• Keywords: Cyclization; Chemical technology; Polyheterocycle; C–H activation; Sulfoximine; TP1-1185; QD415-436; Rhodium catalysis; Biochemistry; 01 natural sciences; 0104 chemical sciences

Disclosed herein is a novel Rh/Ag co-catalyzed SNH directed C–H activation and C–H/N–H bond functionalization protocol of free NH-sulfoximines with hypervalent iodonium ylides. With the aid of AgOTf, these C–H functionalization/cyclization sequences could be achieved at room temperature conditions. The reaction employed EtOH as a “green” solvent and low catalyst loading was required under an oxygen/water-insensitive condition. Under this mild protocol, a wide range of polyheterocyclic sulfoximines bearing fused saturated carbo(hetero)cycles are readily prepared, even toward a complex pharmaceutical Folliculin analog.