Copper-Catalyzed Double Thiolation To Access Sulfur-Bridged Imidazopyridines with Isothiocyanate,The Journal of Organic Chemistry

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Copper-Catalyzed Double Thiolation To Access Sulfur-Bridged Imidazopyridines with Isothiocyanate
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-03-20 00:00:00 , DOI: 10.1021/acs.joc.9b00186
Lu-Lu Tian ₁ , Shuai Lu ₁ , Zhe-Hua Zhang ₁ , En-Ling Huang ₁ , Hua-Ting Yan ₁ , Xinju Zhu ₁ , Xin-Qi Hao ₁ , Mao-Ping Song ₁

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A copper(I)-catalyzed sulfur-bridged dimerization of imidazopyridines has been developed using isothiocyanate as the sulfur source. This method enables a switchable synthesis of bis(imidazo[1,2-a]pyridin-3-yl)sulfanes or bis(2-(imidazo[1,2-a]pyridin-2-yl)phenyl)sulfanes in the presence of 4-dimethylaminopyridine (DMAP) or K₂CO₃ when different imidazopyridines were employed. Under optimized conditions, a variety of sulfur-bridged imidazopyridines were obtained in good yields. Moreover, thiourea was proved to be the key intermediate under catalytic system A.

中文翻译：

铜催化双硫代甲烷与异硫氰酸酯接触硫桥联的咪唑并吡啶

已开发了使用异硫氰酸酯作为硫源的咪唑并吡啶在铜（I）催化下的硫桥联二聚反应。该方法能够在存在下可切换合成双（咪唑并[1,2 - a ]吡啶-3-基）硫烷或双（2-（咪唑并[1,2 - a ]吡啶-2-基]苯基）硫烷当使用不同的咪唑并吡啶时，可以测定4-二甲基氨基吡啶（DMAP）或K ₂ CO _3的含量。在优化的条件下，以高收率获得了各种硫桥联的咪唑并吡啶。此外，已证明硫脲是催化体系A下的关键中间体。

更新日期：2019-03-20

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