Room Temperature ZnBr2‐Catalyzed Regioselective 1,6‐Hydroarylation of Electron‐rich Arenes to para‐Quinone Methides: Synthesis of Unsymmetrical Triarylmethanes
Room Temperature ZnBr2‐Catalyzed Regioselective 1,6‐Hydroarylation of Electron‐rich Arenes to para‐Quinone Methides: Synthesis of Unsymmetrical Triarylmethanes
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室温 ZnBr2 — 催化富电子芳烃区域选择性 1,6 — 氢芳基化生成对醌甲基化物：不对称三芳基甲烷的合成
DOI：
10.1002/asia.202201156
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发表时间：
2023
期刊：
影响因子：
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通讯作者：
Wai-Yeung Wong
中科院分区：
文献类型：
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作者：
Biquan Xiong;Lulu Si;Longzhi Zhu;Rong Wu;Yu Liu;Weifeng Xu;Fan Zhang;Ke-Wen Tang;Wai-Yeung Wong
报道了一种温和高效的锌（II）催化富电子芳烃对醌类化合物（p - QMs）的区域选择性1,6氢化芳基化反应。多种富电子芳烃和对醌类化合物在温和的条件下具有良好的耐受性，以优异的产率提供广泛的三芳基甲烷。本方法也适用于与苯胺、吲哚和苯酚衍生物等其他亲核试剂的氢芳基化反应，在标准条件下可得到相应的三芳基甲烷。通过一步一步的控制实验探索了氢芳基化反应中C(sp3)−C（sp2）键形成的可能机制，并且在化学动力学研究中该反应可能遵循二级方式。
A mild and efficient Zn(II)‐catalyzed regioselective 1,6‐hydroarylation ofpara‐quinone methides (p‐QMs) with electron‐rich arenes protocol is reported. A variety of electron‐rich arenes andpara‐quinone methides are well tolerated under mild conditions, delivering a broad range of triarylmethanes in good to excellent yields. The present method also works well for the hydroarylation ofp‐QMs with other nucleophiles, such as aniline, indole and phenol derivatives, offering the corresponding triarylmethanes with good yields under the standard conditions. The possible mechanism for the formation of C(sp3)−C(sp2) bonds in hydroarylation reactions has been explored by step‐by‐step control experiments, and the reaction may follow a second‐order manner in a chemical kinetic study.