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Regiocontrolled Synthesis of α‑Sulfonylmethyl o‑Nitrostyrenes via ZnI2‑Mediated Sulfonylation and AgNO2/Pd(PPh3)4‑Promoted o‑Nitration

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posted on 2017-09-19, 00:00 authored by Meng-Yang Chang, Han-Yu Chen, Heui-Sin Wang
We report herein the AgNO2/Pd­(PPh3)4-promoted regiocontrolled o-nitration of α-sulfonylmethylstyrenes in MeNO2 with good yields. The o-nitration process provides a series of sulfonyl o-nitrostyrenes. Substituted α-sulfonylmethylstyrenes were synthesized from ZnI2-mediated sulfonylation of substituted α-methylstyrenes and sodium sulfinates (RSO2Na) in MeCN with good to excellent yields. The structures of the key products were confirmed by X-ray crystallography. A plausible mechanism has been proposed herein.

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