Transition-Metal-Free C-H Hydroxylation of Carbonyl Compounds

被引：91

作者：

Chaudhari, Moreshwar B. ^{[1
]}

Sutar, Yogesh ^{[1
]}

Malpathak, Shreyas ^{[1
]}

Hazra, Anirban ^{[1
]}

Gnanaprakasam, Boopathy ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res, Dept Chem, Pune 411008, Maharashtra, India

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 13期

关键词：

ENANTIOSELECTIVE ALPHA-HYDROXYLATION; BIFUNCTIONAL ORGANOCATALYST; ASYMMETRIC HYDROXYLATION; OXINDOLE DERIVATIVES; CATALYZED OXIDATION; OXYGEN; KETONES; OXAZIRIDINE; MECHANISM; CLEAVAGE;

D O I：

10.1021/acs.orglett.7b01616

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transition metal and reductant free alpha-C(sp3)-H hydroxylation of carbonyl compounds are reported. This method is promoted by commercially available inexpensive KO-t-Bu and atmospheric air as an oxidant at room temperature. This unified strategy is also very facile for hydroxylation of various carbonyl compound derivatives to obtain quaternary hydroxyl compounds in excellent yield. A preliminary mechanistic investigation, supported by isotope labeling and computational studies, suggests the formation of a peroxide bond and its cleavage by in situ generated enolate.

引用

页码：3628 / 3631

页数：4

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