Calixarene-supported Pd–NHC complexes as efficient catalysts for scalable Suzuki–Miyaura cross-couplings,Reaction Chemistry & Engineering

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Calixarene-supported Pd–NHC complexes as efficient catalysts for scalable Suzuki–Miyaura cross-couplings
Reaction Chemistry & Engineering ( IF 3.4 ) Pub Date : 2020-07-06 , DOI: 10.1039/d0re00118j
Axel Labattut _{1,

2,

3,

4,

5} , Sandra Abi Fayssal _{1,

2,

3,

4,

5} , Julien Buendia _{5,

6,

7} , Ibrahim Abdellah _{1,

2,

3,

4,

5} , Vincent Huc _{1,

2,

3,

4,

5} , Cyril Martini _{5,

6,

7} , Emmanuelle Schulz _{1,

2,

3,

4,

5}

Affiliation

Benzyloxycalix[8]arene is reported as a suitable macrocyclic support for Pd–NHC complexes, which catalyses C–C cross-coupling reactions with high efficiency. Resulting PEPPSI-derived complexes, issued from a scalable synthetic procedure avoiding any tedious purification, are indeed used as heterogeneous catalysts in ethanol to promote the Suzuki–Miyaura coupling between various aryl halides and arylboronic acids (or esters). Optimisation of the reaction conditions allowed the use of only a slight excess of base (K₃PO₄, 1.2 equivalents) and boronic acid (1.1 equivalents), and these conditions were also successfully applied to a large scale benchmark reaction (1 mole of substrate) using a low palladium loading (0.001 mol%). Furthermore, target products were easily isolated after simple filtration procedures with low residual Pd traces (down to 3 ppm) thanks to the insoluble nature of the macrocyclic catalyst in ethanol, thus proving the usefulness of this support to promote coupling reactions relevant to the fine chemical industry.

中文翻译：

杯芳烃支持的Pd–NHC复合物是可扩展的Suzuki–Miyaura交叉偶联的有效催化剂

据报道，苄氧基杯[8]芳烃是Pd-NHC配合物的合适大环载体，可高效催化CC交叉偶联反应。所得的PEPPSI衍生的复合物，是通过可扩展的合成方法制得的，避免了繁琐的纯化工作，实际上已用作乙醇中的多相催化剂，以促进各种芳基卤化物与芳基硼酸（或酯）之间的Suzuki-Miyaura偶联。反应条件的优化允许仅使用稍微过量的碱（K ₃ PO ₄，1.2当量）和硼酸（1.1当量），并且这些条件也成功地应用于低钯载量（0.001摩尔％）的大规模基准反应（1摩尔底物）。此外，由于大环催化剂在乙醇中的不溶性，在简单的过滤程序后，残留的痕量钯含量低（低至3 ppm），目标产物易于分离，因此证明了这种载体对促进与精细化学品有关的偶联反应的有效性行业。

更新日期：2020-07-28

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