Steric Control of Site Selectivity in the Pd-Catalyzed C-H Acetoxylation of Simple Arenes

被引：71

作者：

Cook, Amanda K. ^{[1
]}

Emmert, Marion H. ^{[1
]}

Sanford, Melanie S. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 21期

基金：

美国国家科学基金会;

关键词：

ELECTRON-DEFICIENT ARENES; POTASSIUM PEROXYDISULFATE; AROMATIC ACETOXYLATION; BOND FUNCTIONALIZATION; PALLADIUM(II) ACETATE; NATURAL-PRODUCTS; PYRIDINE LIGANDS; ACETIC-ACID; ACTIVATION; COMPLEXES;

D O I：

10.1021/ol4024248

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report describes the use of an oxidant and a ligand to control site selectivity in the Pd(OAc)(2)-catalyzed C-H acetoxylation of simple arenes. The use of Mesl(OAc)(2) as the terminal oxidant in combination with acridine as the ligand results in primarily sterically controlled selectivity. In contrast, with Pd(OAc)(2) as the catalyst and Phl(OAc)(2) as the oxidant, electronic effects dominate the selectivity of arene C-H acetoxylation.

引用

页码：5428 / 5431

页数：4

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