Auto-oxidative hydroxysulfenylation of alkenes.
Auto-oxidative hydroxysulfenylation of alkenes.
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DOI：
10.1039/c6cc01937d
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发表时间：
2016-05
影响因子：
4.9
通讯作者：
Congde Huo;Yajun Wang;Yong Yuan;F. Chen;Jing Tang
中科院分区：
文献类型：
--
作者：
Congde Huo;Yajun Wang;Yong Yuan;F. Chen;Jing Tang
探索了缺电子和富电子烯烃与苯硫醇的一锅自动氧化介导的羟基磺基化反应。该方法说明了在温和的无过渡金属条件下，使用 O2 作为氧化剂和氧源，选择性且方便地合成复杂的 β-羟基硫化物。这种新方法在抗癌药物比卡鲁胺的克级合成中的应用已经通过两步序列完成，总收率为 71%。提出了一种合理的激进相关机制。
One-pot auto-oxidation mediated hydroxysulfenylation of electron-deficient and electron-rich olefins with phenthiols was explored. The method illustrates a selective and convenient synthesis of complex β-hydroxysulfides using O2 as both the oxidant and the oxygen source under mild transition-metal-free conditions. The application of this new methodology to the gram-scale synthesis of anti-cancer drug bicalutamide has been accomplished in a two-step sequence with 71% overall yield. A plausible radical involved mechanism is proposed.