Rhodium(III) Catalyzed Carboamination of Alkenes Triggered by C-H Activation of N-Phenoxyacetamides under Redox-Neutral Conditions

被引：67

作者：

Hu, Zhiyong ^{[1
,2
,3
]}

Tong, Xiaofeng ^{[2
,3
]}

Liu, Guixia ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[3] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 07期

基金：

中国国家自然科学基金;

关键词：

OXIDIZING DIRECTING GROUP; INTRAMOLECULAR CARBOAMINATION; BOND ACTIVATION; ROOM-TEMPERATURE; OXIME ESTERS; RH-III; FUNCTIONALIZATION; COMPLEXES; OXIDANT; ACIDS;

D O I：

10.1021/acs.orglett.6b00616

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Alkoxyacrylamides are coupled with N-phenoxyacetamides by Rh-III catalysis through C-H functionalization and amido group transfer under external oxidant-free conditions, which affords acyclic alkene carboamination products in an atom-economical way. Mechanistic insight into this transformation indicates the amide group in N-alkoxyacrylamide plays a critical role in this C-C/C-N bond formation reaction. This methodology provides a highly efficient way to construct o-tyrosine derivatives under mild conditions.

引用

收藏

页码：1702 / 1705

页数：4

相关论文

共 69 条

[61] Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes [J].

Zeng, Wei ;

Chemler, Sherry R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) :12948-+

[62] Rhodium(III)-Catalyzed Transannulation of Cyclopropenes with N-Phenoxyacetamides through C-H Activation [J].

Zhang, Hang ;

Wang, Kang ;

Wang, Bo ;

Yi, Heng ;

Hu, Fangdong ;

Li, Changkun ;

Zhang, Yan ;

Wang, Jianbo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) :13234-13238

[63] Transition metal-catalyzed direct nucleophilic addition of C-H bonds to carbon-heteroatom double bonds [J].

Zhang, Xi-Sha ;

Chen, Kang ;

Shi, Zhang-Jie .

CHEMICAL SCIENCE, 2014, 5 (06) :2146-2159

[64] Rhodium(III)-Catalyzed Cyclative Capture Approach to Diverse 1-Aminoindoline Derivatives at Room Temperature [J].

Zhao, Dongbing ;

Vasquez-Cespedes, Suhelen ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) :1657-1661

[65] Rh(III)-catalyzed C-H functionalization/aromatization cascade with 1,3-dienes: a redox-neutral and regioselective access to isoquinolines [J].

Zhao, Dongbing ;

Lied, Fabian ;

Glorius, Frank .

CHEMICAL SCIENCE, 2014, 5 (07) :2869-2873

[66] Mild and Efficient Ir(III)-Catalyzed Direct C-H Alkynylation of N-Phenoxyacetamides with Terminal Alkyne [J].

Zhou, Jie ;

Shi, Jingjing ;

Qi, Zisong ;

Li, Xingwei ;

Xu, H. Eric ;

Yi, Wei .

ACS CATALYSIS, 2015, 5 (11) :6999-7003

[67] Rh(III)-catalyzed and alcohol-involved carbenoid C-H insertion into N-phenoxyacetamides using α-diazomalonates [J].

Zhou, Jie ;

Shi, Jingjing ;

Liu, Xuelei ;

Jia, Jinlong ;

Song, Huacan ;

Xu, H. Eric ;

Yi, Wei .

CHEMICAL COMMUNICATIONS, 2015, 51 (27) :5868-5871

[68] Cascade Synthesis of 3-Alkylidene Dihydrobenzofuran Derivatives via Rhodium(III)-Catalyzed Redox-Neutral C-H Functionalization/Cyclization [J].

Zhou, Zhi ;

Liu, Guixia ;

Chen, Yan ;

Lu, Xiyan .

ORGANIC LETTERS, 2015, 17 (23) :5874-5877

[69] Synthesis of benzofurans via ruthenium-catalyzed redox-neutral C-H functionalization and reaction with alkynes under mild conditions [J].

Zhou, Zhi ;

Liu, Guixia ;

Shen, Yangyang ;

Lu, Xiyan .

Organic Chemistry Frontiers, 2014, 1 (10) :1161-1165

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