Transition-Metal-Assisted Radical/Radical Cross-Coupling: A New Strategy to the Oxidative C(sp3)-H/N-H Cross-Coupling

被引：151

作者：

Zhou, Liangliang ^{[1
]}

Tang, Shan ^{[1
]}

Qi, Xiaotian ^{[2
]}

Lin, Caitao ^{[1
]}

Liu, Kun ^{[1
]}

Liu, Chao ^{[1
]}

Lan, Yu ^{[2
]}

Lei, Aiwen ^{[1
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

[2] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 12期

基金：

中国国家自然科学基金; 高等学校博士学科点专项科研基金;

关键词：

C-H AMINATION; COPPER-CATALYZED AMIDATION; NITROGEN BOND FORMATION; REDUCTIVE-ELIMINATION; EFFICIENT SYNTHESIS; CARBON; CYCLIZATION; ADJACENT; ETHERS; RUTHENIUM;

D O I：

10.1021/ol501485f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition-metal-assisted oxidative C(sp(3))-H/N-H cross-coupling reaction of N-alkoxyamides with aliphatic hydrocarbons is described. During the reaction, nitrogen radicals were generated from the oxidation of N-alkoxyamides. Experiments and DFT calculations revealed that transition-metal catalyst could lower the reactivity of the generated nitrogen radical by the coordination of the transition metal, which allowed the selective radical/radical cross-coupling with the transient sp(3) carbon radical to construct C(sp(3))--N bonds. Various C(sp(3))-H bonds could be transformed into C(sp(3))-N bonds through this radical amidation strategy.

引用

页码：3404 / 3407

页数：4

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