室温下通过自由基交叉偶联实现吡唑并[1,5 - ]嘧啶的电化学区域选择性C(sp)-H键硫属化反应
Electrochemical Regioselective C(sp)-H Bond Chalcogenation of Pyrazolo[1,5-]pyrimidines via Radical Cross-Coupling at Room Temperature.
作者信息
Chillal Abhinay S, Bhawale Rajesh T, Sharma Siddharth, Kshirsagar Umesh A
机构信息
Department of Chemistry, Indian Institute of Technology Indore, Khandwa Road, Indore 453552, India.
Department of Chemistry, Mohanlal Sukhadia University, Udaipur 313001, India.
出版信息
J Org Chem. 2024 Oct 4;89(19):14496-14504. doi: 10.1021/acs.joc.4c00856. Epub 2024 Sep 16.
Herein, we disclose an electrochemical approach for the C(sp)-H chalcogenation of pyrazolo[1,5-]pyrimidines. This technique offers an oxidant and catalyst-free protocol for achieving regioselective chalcogenation of pyrazolo[1,5-]pyrimidines. The procedure uses only 0.5 equiv. of diaryl chalcogenides which underscores the atom economy of the protocol. Key attributes of this methodology include mild reaction conditions, short reaction time, utilization of cheap electrode materials, and eco-friendly reaction conditions. Cyclic voltammetry studies and radical quenching experiments revealed a radical cross-coupling pathway for the reaction mechanism.
在此，我们公开了一种用于吡唑并[1,5 -]嘧啶的C(sp)-H硫属化的电化学方法。该技术提供了一种无氧化剂和催化剂的方案，用于实现吡唑并[1,5 -]嘧啶的区域选择性硫属化。该方法仅使用0.5当量的二芳基硫属化物，这突出了该方案的原子经济性。该方法的关键特性包括温和的反应条件、短的反应时间、使用廉价的电极材料以及环保的反应条件。循环伏安法研究和自由基猝灭实验揭示了该反应机理的自由基交叉偶联途径。
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