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

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.

本报告介绍了由AgNO2/Pd-(PPh3)4催化的α-磺酰甲基苯乙烯在MeNO2中的区域选择性o-硝化反应，该反应具有良好的产率。该o-硝化过程产生了一系列磺酰o-硝基苯乙烯。通过在MeCN中利用ZnI2介导的磺化反应，从取代的α-甲基苯乙烯和亚硫酸钠（RSO2Na）合成了取代的α-磺酰甲基苯乙烯，产率良好至优秀。关键产物的结构通过X射线晶体学得到了确认。本文提出了一个合理的反应机理。