Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents

被引：34

作者：

Donslund, Aske S. ^{[1
,2
]}

Neumann, Karoline T. ^{[1
,2
]}

Corneliussen, Nicklas P. ^{[1
,2
]}

Grove, Ebbe K. ^{[1
,2
]}

Herbstritt, Domenique ^{[1
,2
]}

Daasbjerg, Kim ^{[1
,2
]}

Skrydstrup, Troels ^{[1
,2
]}

机构：

[1] Aarhus Univ, Dept Chem, Carbon Dioxide Activat Ctr CADIAC, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark

[2] Aarhus Univ, Interdisciplinary Nanosci Ctr iNANO, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 42期

基金：

新加坡国家研究基金会;

关键词：

alkylzinc reagents; beta-ketonitriles; carbonylation; isotope labeling; nickel catalysis; BIMETALLIC OXIDATIVE ADDITION; EFFICIENT SYNTHESIS; METALATED NITRILES; ORGANIC HALIDES; OXONITRILES; BENZOYLACETONITRILES; ARYLATION; EXCHANGE; KETONES; IMINES;

D O I：

10.1002/chem.201902206

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report a nickel-catalyzed carbonylative coupling of alpha-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give beta-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of C-13-labeled beta-ketonitriles and their transformation into isotopically labeled heterocycles.

引用

页码：9856 / 9860

页数：5

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