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Electrochemical oxidative radical oxysulfuration of styrene derivatives with thiols and nucleophilic oxygen sources
Green Chemistry ( IF 9.8 ) Pub Date : 2018-06-22 , DOI: 10.1039/c8gc01337c
Yang Wang 1, 2, 3, 4, 5 , Lingling Deng 1, 2, 3, 4, 5 , Haibo Mei 1, 2, 3, 4, 5 , Bingnan Du 6, 7, 8 , Jianlin Han 1, 2, 3, 4, 5 , Yi Pan 1, 2, 3, 4, 5
Affiliation  

Oxydifunctionalization of olefins represents a powerful tool and yet poses a challenging task. Previous methods have usually required a stoichiometric amount of a strong oxidant and an expensive transition-metal catalyst. This work describes the first example of the electrochemical oxysulfuration reaction of olefins with thiols and nucleophilic oxygen sources. This electrochemical difunctionalization reaction is conducted under catalyst- and oxidant-free conditions, and shows good substrate generality, affording thio-substituted alcohols, ethers and γ-lactones in good chemical yields and with excellent regioselectivities. This work represents a new and green strategy for the difunctionalization of olefins, and also provides a complementary and highly valuable prospect for current methodologies for the synthesis of thio-substituted compounds.

中文翻译:

含硫醇和亲核氧源的苯乙烯衍生物的电化学氧化自由基氧硫化

烯烃的氧二官能化代表了一种强大的工具,但提出了一项艰巨的任务。先前的方法通常需要化学计量的强氧化剂和昂贵的过渡金属催化剂。这项工作描述了烯烃与硫醇和亲核氧源的电化学氧硫化反应的第一个例子。该电化学双官能化反应在无催化剂和无氧化剂的条件下进行,显示出良好的底物通用性,以良好的化学收率和优异的区域选择性提供了硫代取代的醇,醚和γ-内酯。这项工作代表了烯烃双官能化的一种新的绿色策略,并且为目前合成硫代取代化合物的方法学提供了补充和高度有价值的前景。
更新日期:2018-07-30
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