RhII-Catalyzed β-C(sp2)-H Alkylation of Enol Ethers, Enamides and Enecarbamates with α-Diazo Dicarbonyl Compounds

被引：9

作者：

McLarney, Brett D. ^{[1
]}

Cavitt, Marchello A. ^{[1
]}

Donnell, Theodore M. ^{[1
]}

Musaev, Djamaladdin G. ^{[3
]}

France, Stefan ^{[1
,2
]}

机构：

[1] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

[2] Georgia Inst Technol, Petit Inst Bioengn & Biosci, Atlanta, GA 30332 USA

[3] Emory Univ, Cherry L Emerson Ctr Sci Computat, Atlanta, GA 30332 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 05期

基金：

美国国家科学基金会;

关键词：

addition/elimination; alkylation; C-H activation; diazo compounds; rhodium; EFFECTIVE CORE POTENTIALS; DIMETHYL DIAZOMALONATE; MOLECULAR CALCULATIONS; REACTION COORDINATE; ENAMINES; FUNCTIONALIZATION; ARYLDIAZOACETATES; DIHYDROFURANS; REARRANGEMENT; HYBRIDIZATION;

D O I：

10.1002/chem.201604518

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Rh-II-catalyzed method for intermolecular alkylation of the beta-C(sp(2))-H bond of enol ethers, enamides, and enecarbamates with alpha-diazo-1,3-dicarbonyl compounds is reported. The products are formed in up to 99% yield and can be readily derivatized under a variety of conditions. By utilizing a combination of experimental and computational studies, the presumptive addition-elimination reaction mechanism was investigated and found to proceed under thermodynamic control at higher temperature. The acquired fundamental knowledge was translated into a strategic reaction design and yielded the first example of the beta-C-H functionalizations of acyclic enol ethers using a-diazo-1,3-dicarbonyl compounds.

引用

页码：1129 / 1135

页数：7

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