氰化
化学
催化作用
氰化物
芳基
镍
溴化物
卤化物
达布科
溶解
盐(化学)
同种类的
无机化学
辛烷值
有机化学
药物化学
物理
热力学
烷基
作者
Geraldo Duran-Camacho,J. Caleb Hethcox
出处
期刊:Organic Letters
[American Chemical Society]
日期:2022-11-09
卷期号:24 (45): 8397-8400
被引量:1
标识
DOI:10.1021/acs.orglett.2c03503
摘要
A nickel-catalyzed cyanation of (hetero)aryl halides using air-stable bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane (DABAL-Me3) as a soluble reductant has been developed. The reaction uses readily available and inexpensive Ni(dppf)Cl2 as a precatalyst, a substoichiometric amount of Zn(CN)2, and DABAL-Me3 as an alternative to commonly prescribed insoluble reductants. We found the addition of catalytic tetrabutylammonium bromide (TBABr) to be beneficial, due to facilitating dissolution of low levels of the cyanide salt (confirmed via a control study). Similarly, slow addition of a tetrabutylammonium cyanide (TBACN) solution is effective and results in a completely homogeneous reaction mixture.
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