Zhang Jianping, Chen Ziyan, Chen Mingxin, Zhou Qi, Zhou Rongrong, Wang Wenli, Shao Yinlin, Zhang Fangjun
School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China.
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
J Org Chem. 2024 Jan 19;89(2):887-897. doi: 10.1021/acs.joc.3c01767. Epub 2024 Jan 4.
We have developed a lanthanide/B(CF)-promoted hydroboration reduction of indoles and quinolines with pinacolborane (HBpin). This reaction provides streamlined access to a range of nitrogen-containing compounds in moderate to excellent yields. Large-scale synthesis and further transformations to bioactive compounds indicate that the method has potential practical applications. Preliminary mechanistic studies suggest that amine additives promote the formation of indole-borane intermediates, and the lanthanide/B(CF)-promoted hydroboration reduction proceeds via hydroboration of indole-borane intermediates with HBpin and in situ-formed BH species, followed by the protodeborylation process.
