Electrochemical Ruthenium-Catalyzed C-H Hydroxylation of Amine Derivatives in Aqueous Acid

被引：22
|
作者：
Robinson, Sophia G. [1 ]
Mack, James B. C. [2 ]
Alektiar, Sara N. [1 ]
Du Bois, J. [2 ]
Sigman, Matthew S. [1 ]
机构：
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
[2] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 18期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
FUNCTIONALIZATION; DEHYDROGENATION; OXYGENATION; OXIDATION; TERTIARY; BONDS;
D O I：
10.1021/acs.orglett.0c01313
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of an electrochemically driven, ruthenium-catalyzed C-H hydroxylation reaction of amine-derived substrates bearing tertiary C-H bonds is described. The reaction is performed under constant current electrolysis in a divided cell to afford alcohol products in yields comparable to those of our previously reported process, which requires the use of stoichiometric H5IO6 for catalytic turnover. With aqueous acid as solvent, the cathodic electrode reaction simply involves the reduction of protons to evolve hydrogen gas. The optimized protocol offers a convenient, efficient, and atom-economical method for sp(3)-C-H bond oxidation.
引用
收藏
页码：7060 / 7063
页数：4
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