First C-H Activation Route to Oxindoles using Copper Catalysis

被引：164

作者：

Klein, Johannes E. M. N. ^{[1
]}

Perry, Alexis ^{[1
]}

Pugh, David S. ^{[1
]}

Taylor, Richard J. K. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 15期

基金：

英国工程与自然科学研究理事会;

关键词：

CARBON BOND FORMATION; INTRAMOLECULAR CYANOAMIDATION; DERIVATIVES; AGENTS;

D O I：

10.1021/ol1012668

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of 3,3-disubstituted oxindoles by a formal C-H, Ar-H coupling of anilides is described. Highly efficient conditions have been Identified using catalytic (5 mol %) Cu(OAc)(2)center dot H(2)O with atmospheric oxygen as the reoxidant; no additional base is required, and the reaction can be run in toluene or mesitylene. Optimization studies are reported together with a scope and limitation investigation based on variation of the anilide precursors. The application of this methodology to prepare a key Intermediate for the total synthesis of the anticancer, analgesic oxindole alkaloid Horsfiline is also described.

引用

页码：3446 / 3449

页数：4

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