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(DMP)DAB–Pd–MAH: A Versatile Pd(0) Source for Precatalyst Formation, Reaction Screening, and Preparative-Scale Synthesis
ChemRxiv Pub Date : 2021-01-20
Jingjun Huang, Matthew Isaac, Ryan Watt, Joseph Becica, Emma Dennis, Makhsud I. Saidaminov, William A. Sabbers, David Leitch

We report an easily prepared and bench-stable mononuclear Pd(0) source stabilized by a chelating N,N’-diaryldiazabutadiene ligand and maleic anhydride: DMPDAB–Pd–MAH. Phosphine ligands of all types, including bidentate phosphines and large cone angle biarylphosphines, rapidly and completely displace the diazabutadiene ligand at room temperature to give air-stable Pd(0) phosphine complexes. DMPDAB–Pd–MAH itself is readily soluble and stable in several organic solvents, making it an ideal Pd source for in situ catalyst preparation during reaction screening, as well as solution-dispensing to plate-based reaction arrays for high-throughput experimentation. Evaluation of DMPDAB–Pd–MAH alongside other common Pd(0) and Pd(II) sources in microscale reaction screens reveals that DMPDAB–Pd–MAH is superior at identifying hits across six different C–N, C–C, and C–O coupling reactions. DMPDAB–Pd–MAH, and the phosphine precatalysts derived therefrom, are also effective in preparative-scale cross couplings at low Pd loadings.

中文翻译:

(DMP)DAB–Pd–MAH:一种多功能的Pd(0)源,用于催化剂前的形成,反应筛选和制备规模的合成

我们报告了一种易于制备且稳定的单核Pd(0)源,其通过N,N'-二芳基二氮杂丁二烯配体和顺丁烯二酸酐的螯合来稳定:DMPDAB–Pd–MAH。包括二齿膦和大锥角联芳膦在内的所有类型的膦配体,在室温下都能快速,完全地置换二氮杂丁二烯配体,从而形成空气稳定的Pd(0)膦配合物。DMPDAB–Pd–MAH本身易溶于多种有机溶剂中并稳定,使其成为反应筛选过程中原位催化剂制备以及溶液分配至板式反应阵列进行高通量实验的理想Pd来源。在微型反应筛中对DMPDAB–Pd–MAH和其他常见Pd(0)和Pd(II)来源的评估显示,DMPDAB–Pd–MAH在识别六种不同C–N,CC–C,和CO偶联反应。DMPDAB–Pd–MAH和由其衍生的膦预催化剂在低Pd负载量下也可用于制备规模的交叉偶联。
更新日期:2021-01-20
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