Rh(II)-catalyzed Intermolecular Benzylic C(sp3)-H Alkylation of Methyl-substituted Arenes by N-Aryl-α-diazo-β-amidoesters

被引：1
|
作者：
Yuan, Shaoren [1 ]
McLaren, Eric J. [1 ]
France, Stefan [1 ,2 ]
机构：
[1] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA
[2] Georgia Inst Technol, Parker H Petit Inst Bioengn & Biosci, Atlanta, GA 30332 USA
来源：
CHEMCATCHEM | 2022年 / 14卷 / 11期
基金：
美国国家科学基金会;
关键词：
C-H functionalization; dirhodium carbenes; diazo compounds; orthogonality; 1,3-dicarbonyl compounds; PREDICTIVE MODEL; CARBENE; SECONDARY; INSERTION; BONDS;
D O I：
10.1002/cctc.202101977
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Herein, a general approach to intermolecular benzylic C(sp(3)) H alkylation of methyl-substituted arenes is reported using metal carbenes derived from N-aryl-alpha-diazo-beta-amidoesters and dirhodium catalysts. Alkylated products were formed in up to 81 % yield with demonstrated functional group tolerance, outpacing previous literature. The unique amide-ester scaffolding can be exploited through various derivatizations for broad synthetic utility and provides a starting point for the development of selectivity rules and reactivity profiles for these intermolecular C(sp(3)) H functionalizations.
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页数：6
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