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

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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.