Accessing para-Alkylphenols via Iridium-Catalyzed Site-Specific Deoxygenation of Alcohols

被引：12

作者：

Wang, Jing ^{[1
]}

Wang, Tingting ^{[1
]}

Du, Hongguang ^{[1
]}

Chen, Ning ^{[1
]}

Xu, Jiaxi ^{[1
]}

Yang, Zhanhui ^{[1
]}

机构：

[1] Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 17期

关键词：

PARA-QUINONE METHIDES; FORMIC-ACID; REDUCTION; PHENOLS; IDENTIFICATION; HYDROGENATION; EFFICIENT; DESIGN;

D O I：

10.1021/acs.joc.3c01294

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iridium-catalyzed and phenol-directed deoxygenationof benzylicalcohols comes as an alternative access to 4-alkylphenols, featuringlow catalyst loading (S/C up to20,000, TOF up to 12,400 h(-1)), high functionalitycompatibility, and excellent site-selectivity. The applications inlate-stage modification of steroids and gram-scale total synthesisof a Gastrodia elata extract are highlighted.Mechanistically, the intermediacy of quinone methide controls thesite-selectivity, and the formation of iridium hydride serves as therate-limiting step.

引用

页码：12572 / 12584

页数：13

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