Mechanistic Guidance Leads to Enhanced Site-Selectivity in C-H Oxidation Reactions Catalyzed by Ruthenium bis(Bipyridine) Complexes

被引：24

作者：

Griffin, Jeremy D. ^{[2
]}

Vogt, David B. ^{[2
]}

Du Bois, J. ^{[1
]}

Sigman, Matthew S. ^{[2
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

[2] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

ACS CATALYSIS | 2021年 / 11卷 / 16期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

C-H oxidation; ruthenium; catalysis; regioselective; organic reactions; Bronsted acid; BONDS; FUNCTIONALIZATION; HYDROXYLATION; HYDROCARBONS; OXYFUNCTIONALIZATION; DERIVATIVES; ACTIVATION; DIOXIRANES; TARGETS; REMOTE;

D O I：

10.1021/acscatal.1c02593

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The development of an operationally simple C-H oxidation protocol using an acid-stable, bis(bipyridine)Ru catalyst is described. Electronic differences remote to the site of C-H functionalization are found to affect product selectivity. Site-selectivity is further influenced by the choice of reaction solvent, with highest levels of 2 degrees methylene oxidation favored in aqueous dichloroacetic acid. A statistical model is detailed that correlates product selectivity outcomes with computational parameters describing the relative "electron-richness" of C-H bonds.

引用

收藏

页码：10479 / 10486

页数：8

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