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Synthesis of Pd Complexes Containing Tailed NHC Ligands and Their Use in a Semicontinuous Membrane-Assisted Suzuki Cross-Coupling Process
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-10-02 00:00:00 , DOI: 10.1021/acs.oprd.8b00273 Dominic Ormerod 1 , Matthieu Dorbec 1 , Eugen Merkul 2 , Nadya Kaval 2 , Nicolas Lefèvre 2 , Steven Hostyn 2 , Lies Eykens 1 , Jo Lievens 1 , Sergey Sergeyev 2 , Bert U. W. Maes 2
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-10-02 00:00:00 , DOI: 10.1021/acs.oprd.8b00273 Dominic Ormerod 1 , Matthieu Dorbec 1 , Eugen Merkul 2 , Nadya Kaval 2 , Nicolas Lefèvre 2 , Steven Hostyn 2 , Lies Eykens 1 , Jo Lievens 1 , Sergey Sergeyev 2 , Bert U. W. Maes 2
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Homogeneous catalysis has proved to be a reliable method for preparing numerous molecular entities, but catalysts can be expensive and difficult to remove. Because of this, industry targets catalysts that are easily separated and recovered and feature increased turnover numbers. The ongoing shift from multipurpose batch reactors toward continuous manufacturing in fine chemicals synthesis results in a new set of catalyst requirements. This paper reports the design and use of Pd complexes suitable for a semicontinuous Suzuki cross-coupling reaction based on a membrane-assisted reactor. These Pd complexes contain tailed N-heterocyclic carbene (NHC) ligands, allowing internal catalyst recovery by organic solvent nanofiltration with top-layer-modified ceramic membranes. These membranes give selective nanofiltration of the catalyst based on a combination of size exclusion and affinity separation (solvent–solute–membrane interactions). The semicontinuous system developed led to significantly improved turnover numbers, simplified product isolation, and consequently reduced mass intensity by simply adding more of the reactants and reagents to the reaction vessel.
中文翻译：
含尾部NHC配体的Pd配合物的合成及其在半连续膜辅助Suzuki交叉偶联过程中的应用
均相催化已被证明是制备多种分子实体的可靠方法，但催化剂价格昂贵且难以去除。因此，工业上的目标是容易分离和回收并且具有增加的周转次数的催化剂。从多功能间歇式反应器向精细化学品合成的连续生产的不断转变导致了对催化剂的新要求。本文报道了适用于基于膜辅助反应器的半连续Suzuki交叉偶联反应的Pd配合物的设计和使用。这些Pd配合物包含尾状N-杂环卡宾（NHC）配体，可通过有机溶剂纳米过滤和顶层改性的陶瓷膜进行内部催化剂回收。这些膜基于尺寸排阻和亲和力分离（溶剂-溶质-膜相互作用）的组合，对催化剂进行选择性的纳滤。通过简单地向反应容器中添加更多的反应物和试剂，开发出的半连续系统可显着提高周转次数，简化产品分离并因此降低质量强度。
更新日期：2018-10-02
中文翻译：
含尾部NHC配体的Pd配合物的合成及其在半连续膜辅助Suzuki交叉偶联过程中的应用
均相催化已被证明是制备多种分子实体的可靠方法，但催化剂价格昂贵且难以去除。因此，工业上的目标是容易分离和回收并且具有增加的周转次数的催化剂。从多功能间歇式反应器向精细化学品合成的连续生产的不断转变导致了对催化剂的新要求。本文报道了适用于基于膜辅助反应器的半连续Suzuki交叉偶联反应的Pd配合物的设计和使用。这些Pd配合物包含尾状N-杂环卡宾（NHC）配体，可通过有机溶剂纳米过滤和顶层改性的陶瓷膜进行内部催化剂回收。这些膜基于尺寸排阻和亲和力分离（溶剂-溶质-膜相互作用）的组合，对催化剂进行选择性的纳滤。通过简单地向反应容器中添加更多的反应物和试剂，开发出的半连续系统可显着提高周转次数，简化产品分离并因此降低质量强度。
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