Synthesis of ?-Aryl Secondary Amides via Nickel-Catalyzed Reductive Coupling of Redox-Active Esters

被引：8
|
作者：
Gabbey, Alexis L. [1 ]
Michel, Nicholas W. M. [1 ]
Hughes, Jonathan M. E. [2 ]
Campeau, Louis-Charles [2 ]
Rousseaux, Sophie A. L. [2 ]
机构：
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
[2] Merck & Co Inc, Dept Proc Res & Dev, Rahway, NJ 07065 USA
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 17期
基金：
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词：
INTERMOLECULAR ALPHA-ARYLATION; CROSS-COUPLINGS; BROMO AMIDES; OXINDOLES; HALIDES; REACTIVITY; COMPLEXES; BOND;
D O I：
10.1021/acs.orglett.2c00918
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The transition-metal-catalyzed alpha-arylation of secon-dary amides remains a synthetic challenge due to the presence of afree N-H bond. We report a strategy to synthesize secondary alpha-aryl amides via a Ni-catalyzed reductive arylation of redox-activeN-hydroxyphthalimide (NHP) esters of malonic acid half amides.This transformation proceeds under mild conditions and displaysexcellent chemoselectivity for amide alpha-arylation in the presence ofother enolizable carbonyls. The NHP ester substrates are readily prepared from Meldrum's acid
引用
收藏
页码：3173 / 3178
页数：6
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