Copper-Catalyzed Intermolecular Difunctionalization of Styrenes with Thiosulfonates and Arylboronic Acids via a Radical Relay Pathway
Copper-Catalyzed Intermolecular Difunctionalization of Styrenes with Thiosulfonates and Arylboronic Acids via a Radical Relay Pathway
复制标题
DOI：
10.1021/acscatal.9b04887
复制
发表时间：
2020-02-21
期刊：
影响因子：
12.9
通讯作者：
Jia, Tiezheng
中科院分区：
文献类型：
--
作者：
Liang, Qingjin;Walsh, Patrick J.;Jia, Tiezheng
发展了一种通用的、实用的铜催化苯乙烯与硫代磺酸甲酯和芳基硼酸的分子间双官能化反应策略。该方法提供了从容易获得的甲基硫代磺酸酯和市售的苯乙烯和芳基硼酸衍生物获得宽范围的2，2-二芳基乙基砜衍生物的有效和直接的途径。不同的底物范围证明了该反应的高官能团耐受性。该方法的温和性质使其适用于生物活性天然产物的后期功能化。机制研究支持磺酰基自由基的作用，并证实了铜催化的自由基中继途径。
A general and practical copper-catalyzed intermolecular difunctionalization strategy of styrenes with methyl thiosulfonates and arylboronic acids has been developed. This method provides an efficient and straightforward avenue to a broad range of 2,2-diarylethyl sulfone derivatives from readily available methyl thiosulfonates and commercially available styrene and arylboronic acid derivatives. The diverse substrate scope attests to the high functional group tolerance of this reaction. The mild nature of this protocol make it suitable for late-stage functionalization of bioactive natural products. Mechanistic investigations support the role of sulfonyl radicals and corroborate a copper-catalyzed radical relay pathway.