Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters

被引：27
作者：
Michel, Nicholas W. M. [1 ]
Jeanneret, Alexandria D. M. [1 ]
Kim, Hyehwang [1 ]
Rousseaux, Sophie A. L. [1 ]
机构：
[1] Univ Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期
基金：
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词：
CROSS-COUPLING REACTIONS; ALPHA-ARYL NITRILES; C-O ACTIVATION; TRIMETHYLSILYL CYANIDE; BOND ACTIVATION; INTRAMOLECULAR ARYLCYANATION; ASYMMETRIC HYDROCYANATION; QUATERNARY STEREOCENTERS; KINETIC RESOLUTION; PALLADIUM-COMPLEX;
D O I：
10.1021/acs.joc.8b01763
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)(2). Alkene additives were found to inhibit catalysis, suggesting that avoiding beta-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (+/-)-naproxen from commercially available starting materials.
引用
收藏
页码：11860 / 11872
页数：13
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