Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide

被引：31

作者：

Camelio, Andrew M. ^{[1
]}

Liang, Yong ^{[2
]}

Eliasen, Anders M. ^{[1
,4
]}

Johnson, Trevor C. ^{[1
,4
]}

Yuan, Changxia ^{[1
]}

Schuppe, Alex W. ^{[1
]}

Houk, K. N. ^{[2
,3
]}

Siegel, Dionicio ^{[1
,4
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[3] Univ Calif Los Angeles, Dept Chem & Biomol Engn, Los Angeles, CA 90095 USA

[4] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92037 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 16期

基金：

美国国家科学基金会;

关键词：

CYCLIC DIACYL PEROXIDES; FRIEDEL-CRAFTS OXYGENATION; DIISOPROPYL PEROXYDICARBONATE; HYDROGEN-PEROXIDE; CUPRIC CHLORIDE; AROMATIC OXYGENATION; ACID; OXYFUNCTIONALIZATION; ALKYLBENZENES; HYDROCARBONS;

D O I：

10.1021/acs.joc.5b01079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.

引用

页码：8084 / 8095

页数：12

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