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

页码：1702 / 1705

页数：4

共 69 条

[11]

Endo Y., 1980, SYNTHESIS-STUTTGART, V1980, P461

[12]

Endo Y., 1983, SYNTHESIS-STUTTGART, V1983, P471

[13] Direct Observation of Reductive Elimination of MeX (X = Cl, Br, I) from RhIII Complexes: Mechanistic Insight and the Importance of Sterics [J].