镍催化噻吩通过双C(sp)-H/C(sp)-H键裂解的直接烷基化反应：KHPO的重要性
Nickel-catalysed direct alkylation of thiophenes via double C(sp)-H/C(sp)-H bond cleavage: the importance of KHPO.
作者信息
Wang Xie, Xie Peipei, Qiu Renhua, Zhu Longzhi, Liu Ting, Li You, Iwasaki Takanori, Au Chak-Tong, Xu Xinhua, Xia Yuanzhi, Yin Shuang-Feng, Kambe Nobuaki
机构信息
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China.
出版信息
Chem Commun (Camb). 2017 Jul 20;53(59):8316-8319. doi: 10.1039/c7cc04252c.
A Ni-catalyzed oxidative C-H/C-H cross-dehydrogenative coupling (CDC) reaction was developed for constructing various highly functionalized alkyl (aryl)-substituted thiophenes. This method employs thiophenes and aliphatic (aromatic) amides that contain an 8-aminoquinoline as a removable directing group in the presence of a silver oxidant. The approach enables the facile one-step synthesis of substituted thiophenes with high functional group compatibility via double C-H bond cleavage without affecting C-Br and C-I bonds. DFT calculations verify the importance of KHPO as an additive for promoting C-H bond cleavage and support the involvement of a Ni(iii) species in the reaction.
开发了一种镍催化的氧化C-H/C-H交叉脱氢偶联（CDC）反应，用于构建各种高度官能化的烷基（芳基）取代噻吩。该方法使用噻吩和含有8-氨基喹啉作为可去除导向基团的脂肪族（芳香族）酰胺，在银氧化剂存在下进行反应。该方法能够通过双C-H键裂解，在不影响C-Br和C-I键的情况下，以高官能团兼容性轻松一步合成取代噻吩。密度泛函理论（DFT）计算证实了KHPO作为促进C-H键裂解添加剂的重要性，并支持反应中Ni(III)物种的参与。
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