Benzimidazolyl Palladium Complexes as Highly Active and General Bifunctional Catalysts in Sustainable Cross-Coupling Reactions

Benzimidazolyl Palladium Complexes as Highly Active and General Bifunctional Catalysts in Sustainable Cross-Coupling Reactions
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苯并咪唑基钯配合物作为可持续交叉偶联反应中的高活性和通用双功能催化剂

DOI:
10.1021/acscatal.9b02420
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发表时间:
2019
期刊:
影响因子:
12.9
通讯作者:
V. Lindsay
V. Lindsay
中科院分区:
化学1区
文献类型:
--
作者:
Jiancheng Zhu;V. Lindsay

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报道了一类具有空气和水分稳定性的2-苯并咪唑基双核钯配合物,它们在不同的交叉偶联反应中是一种高效的通用催化平台。通过将2-苯并咪唑基部分拴系到二胺配体上,可以容易地修改配体支架的刚性和构象,从而导致催化活性的显著变化。在最佳条件下,Suzuki,Heck和Sonogashira型偶联的芳基溴都可以有效地进行良好的官能团相容性,仅使用0.1摩尔%的催化剂,在水溶液或醇溶剂。实验证据突出了催化活性的配体的双官能特性的重要性,其中在配体框架中的基本N-官能度被提议通过分子内协助来加速(反式)金属化步骤。
A family of air- and moisture-stable dinuclear palladium complexes bearing 2-benzimidazolyl ligands is reported and shown to be a highly effective and general catalytic platform in diverse cross-coupling reactions. The rigidity and conformation of the ligand scaffold was readily modified via tethering of the 2-benzimidazolyl moiety to diamine ligands, resulting in significant changes in catalytic activity. Under optimal conditions, Suzuki, Heck, and Sonogashira-type couplings of aryl bromides can all be performed efficiently with good functional group compatibility using only 0.1 mol % of catalyst, in aqueous or alcohol solvents. Experimental evidence highlights the importance of the bifunctional character of the ligand for catalytic activity, where the basic N-functionality in the ligand framework is proposed to accelerate (trans)metalation steps via intramolecular assistance.
DOI: 10.1021/jo400159y
发表时间: 2013-09-20
期刊: The Journal of organic chemistry
影响因子: --
作者:
Engle KM;Yu JQ
通讯作者: Yu JQ
DOI: 10.1021/jo0617013
发表时间: 2006-12-22
影响因子: 3.6
作者:
Molander, Gary A.;Brown, Adam R.
通讯作者: Brown, Adam R.