Syntheses of Four-Coordinate Nickel(II)-Phosphine Compounds and a Rapid Suzuki–Miyaura Cross-Coupling Reaction for Short Laboratory Sessions
Syntheses of Four-Coordinate Nickel(II)-Phosphine Compounds and a Rapid Suzuki–Miyaura Cross-Coupling Reaction for Short Laboratory Sessions
复制标题
四配位镍 (II)-膦化合物的合成和快速 Suzuki-Miyaura 交叉偶联反应的短期实验室会议
作者：
J. Cooke
由水合溴化镍和磷化氢制备[NiBr 2（PPh 3）2]和[NiBr 2（dppe）]。这些明亮颜色的配位化合物然后通过与格氏试剂MesMgBr反应转化为相关的有机金属化合物trans-NiBr（Mes）（PPh 3）2]和[NiBr（Mes）（dppe）]（Mes = 2，4，6-Me 3C 6 H2）。化合物的表征通过UV-vis和多核NMR光谱的组合来完成。[NiBr（Mes）（dppe）]是4′-溴苯乙酮与苯硼酸Suzuki-Miyaura偶联反应的高活性预催化剂。催化反应在15-20分钟内完成，预催化剂负载量仅为1摩尔%，并且反应可以在空气中进行。通过1H NMR光谱评估结果，或者可以在水处理和重结晶后分离固体4-乙酰基联苯产物。实验是灵活的，并适应各种实验室的时间表和学生的技能水平。每个实验组件都被设计为在3小时的实验室时间内完成。
[NiBr2(PPh3)2] and [NiBr2(dppe)] are prepared from nickel bromide hydrate and phosphine. These brightly colored coordination compounds are then converted into the related organometallic compounds trans-[NiBr(Mes)(PPh3)2] and [NiBr(Mes)(dppe)] (Mes = 2,4,6-Me3C6H2) by reaction with the Grignard reagent MesMgBr. Characterization of the compounds is accomplished by a combination of UV–vis and multinuclear NMR spectroscopies. [NiBr(Mes)(dppe)] is a highly active precatalyst for the Suzuki–Miyaura cross-coupling of 4′-bromoacetophenone and phenylboronic acid. The catalytic reaction is complete in as little as 15–20 min with only a 1 mol % precatalyst loading, and the reaction can be carried out in air. Results are assessed by 1H NMR spectroscopy, or the solid 4-acetylbiphenyl product can be isolated following aqueous workup and recrystallization. The experiments are flexible and accommodate a variety of laboratory schedules and student skill levels. Each experimental component has been designed to be completed within a 3 h laboratory period.
影响因子：
16.6
作者：
Ge, Shaozhong;Hartwig, John F.
通讯作者：
Hartwig, John F.