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合理探索 N-杂环卡宾(NHC)钯环多样性:一种用于失活芳基和烷基底物的 Suzuki-Miyaura 偶联反应的高活性、多功能前催化剂。

Rational exploration of N-heterocyclic carbene (NHC) palladacycle diversity: a highly active and versatile precatalyst for Suzuki-Miyaura coupling reactions of deactivated aryl and alkyl substrates.

机构信息

Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos, Singapore 138669, Singapore.

出版信息

Chemistry. 2010 Apr 6;16(13):4010-7. doi: 10.1002/chem.200902842.

DOI:10.1002/chem.200902842
PMID:20175159
Abstract

As less attention has been focussed on the design of highly efficient palladium precatalysts to ensure the smooth formation of the active catalyst for metal-mediated cross coupling reactions, we herein demonstrate that combining the bulky N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) with cyclopalladated acetanilide as the optimal palladium precatalyst leads to superior catalytic activity compared with the state-of-the-art NHC-Pd catalysts. The complex was discovered through the evaluation of a small, rationally designed library of NHC-palladacycles prepared by a novel, practical and atom-economic method, the direct reaction of IPrHCl with palladacycle acetate dimers.

摘要

由于人们对高效钯前催化剂的设计关注较少,无法确保用于介导金属交叉偶联反应的活性催化剂的顺利形成,因此我们在此证明,将大位阻的 N-杂环卡宾(NHC)1,3-双(2,6-二异丙基苯基)咪唑-2-亚基(IPr)与环钯化乙酰胺结合作为最佳钯前催化剂,与最先进的 NHC-Pd 催化剂相比,具有更高的催化活性。该配合物是通过对一小部分通过新型、实用且原子经济性的方法——IPrHCl 与钯环二聚体的直接反应制备的、经过合理设计的 NHC-钯环的文库进行评估而发现的。

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