Hydroxymethylation of quinolines via iron promoted oxidative C-H functionalization: synthesis of arsindoline-A and its derivatives

Herein, we report a mild and efficient hydroxymethylation of quinolines via an iron promoted cross-dehydrogenative coupling reaction under external acid free conditions. Various hydroxyalkyl substituted quinolines were achieved in excellent yields with well tolerated functional groups. Importantly, a few of the hydroxylmethylated quinolines were further transformed into respective aldehydes, and were successfully utilized for the synthesis of alkaloid arsindoline-A and its derivatives.

Automated summary

This study presents a mild and efficient hydroxymethylation reaction of quinolines under external acid free conditions via an iron promoted cross-dehydrogenative coupling reaction, yielding various hydroxyalkyl substituted quinolines with excellent yields and well tolerated functional groups. Some of the hydroxylmethylated quinolines were further transformed into aldehydes, which were successfully utilized for the synthesis of alkaloid arsindoline-A and its derivatives.