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

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

doi:10.1021/acs.joc.3c02108.s001

jo3c02108_si_001.pdf (4.63 MB)

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

journal contribution

posted on 2023-12-14, 21:07 authored by Changyuan Zhang, Jianping Lin, Li Wang, Yingxuan Mei, Lanjing Wang, Yuqing Xie, Yu Lu, Jiakai Tian, Wei Wang, Lulu Chen, Mengping Guo, Cailong Zhou

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.