Zhao Yaokun, Li Xingchi, Zhou Pengfei, Han Xing, Zhang Chenjie, Liang Taoyuan, Zhao Shuangliang, Zhang Zhuan
Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, China.
Org Lett. 2024 Sep 6;26(35):7285-7290. doi: 10.1021/acs.orglett.4c02151. Epub 2024 Aug 23.
We have disclosed silver(I)-induced switching of regioselectivity in rhodium-catalyzed C-H alkynylation of indole derivatives with the help of a pivaloyl directing group by tuning C-H metalation modes. The judicious choice of AgOAc, AgO, and AgCO affords an array of C2-alkynylated indoles, C4-alkynylated indoles, and C2,C4-dialkynylated indoles, respectively. The synthetic utility of the alkyne fragment is demonstrated by derivatization into valuable indole-based compounds.
我们已经揭示了在新戊酰基导向基团的帮助下，通过调节C-H金属化模式，银（I）可诱导铑催化的吲哚衍生物的C-H炔基化反应区域选择性发生转变。通过明智地选择醋酸银、氧化银和碳酸银，分别得到了一系列C2-炔基化吲哚、C4-炔基化吲哚和C2,C4-二炔基化吲哚。通过将炔烃片段衍生为有价值的基于吲哚的化合物，证明了其合成实用性。
