Tf2O-Mediated Tandem Reaction of Enaminones for the Synthesis of Functionalized Conjugated-Enals/β-Naphthalaldehydes

Changyuan Zhang; Jianping Lin; Li Wang; Yingxuan Mei; Lanjing Wang; Yuqing Xie; Yu Lu; Jiakai Tian; Wei Wang; Lulu Chen; Mengping Guo; Cailong Zhou

doi:10.1021/acs.joc.3c02108

Tf₂O-Mediated Tandem Reaction of Enaminones for the Synthesis of Functionalized Conjugated-Enals/β-Naphthalaldehydes

J Org Chem. 2024 Jan 5;89(1):373-378. doi: 10.1021/acs.joc.3c02108. Epub 2023 Dec 14.

Authors

Changyuan Zhang¹, Jianping Lin¹, Li Wang¹, Yingxuan Mei^{1

2}, Lanjing Wang¹, Yuqing Xie¹, Yu Lu¹, Jiakai Tian¹, Wei Wang¹, Lulu Chen¹, Mengping Guo¹, Cailong Zhou³

Affiliations

¹ Key Laboratory of Jiangxi University for Applied Chemistry and Chemical Biology, College of Chemistry and Bio-engineering, Yichun University, Yichun 336000, P. R. China.
² Department of Basic Medicine, Yichun Vocational Technical College, Yichun 336000, P. R. China.
³ School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, P. R. China.

PMID: 38096478
DOI: 10.1021/acs.joc.3c02108

Abstract

A highly efficient and regioselective method for constructing functionalized conjugated enals via the Tf₂O-mediated tandem reaction of enaminones with thiophenols has been described. Chain products with excellent stereoselectivity could be obtained through substrate regulation. Additionally, a feasible method for synthesizing β-naphthalaldehydes through PhSO₂Na/DABCO promoting hydrogen atom transfer process has also been reported here. Mechanism studies have shown that 2-formyl vinyl triflate 8 and sulfonylated enal 9 were the key intermediates in this process.