文献类型：期刊文献

英文题名：Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes

作者：Liu, Yonghai[1,2];Yu, Yang[1,2];Sun, Chengyu[1,2];Fu, Yiwei[1,2];Mang, Zhiguo[1,2];Shi, Lei[3];Li, Hao[1,2]

机构：[1]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[3]Firmenich Aromat China Co Ltd, Corp R&D Div, Shanghai 201108, Peoples R China

年份：2020

卷号：22

期号：20

起止页码：8127

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000623541500004)，CCR-EXPANDED(收录号:WOS:000623541500004)】；

基金：This work was supported by the National Natural Science Foundation of China (21572054), the program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the Fundamental Research Funds for the Central Universities, and the China 111 Project (Grant B07023).

语种：英文

摘要：We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d(6), this protocol resulted in difunctionalization of heterobenzylic methylenes to afford a-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.