Development of chiral modular bifunctional C2-symmetric bipyridine/phenanthroline-bipyrroloimidazolone ligands and application in noncovalent interaction-assisted enantioselective catalysis†

IF 2.7 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY New Journal of Chemistry Pub Date : 2024-12-30 DOI:10.1039/D4NJ05018E
Xi-Rui Wang, Pan Hu, Hui-Xian Jing, Zhang-Biao Yu, Zhen Yao, Xiong-Wei Liu, Wen-Jing Zhang, Li-Jun Peng and Xiong-Li Liu
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Abstract

Chiral bipyridine/phenanthroline ligands have been applied as a class of unique ligands due to their rich coordination chemistry in catalysis. Herein, we synthesize 13 new C2-symmetric chiral phenanthroline-bipyrroloimidazolone ligands (Phen-BPI) and 5 new C2-symmetric chiral bipyridine-bipyrroloimidazolone ligands (BPy-BPI). These Bpy/Phen-BPI pincer ligands performed successfully in nickel-catalyzed asymmetric Friedel–Crafts alkylation of indoles with 2-enoylpyridine-1-oxides, affording the chiral products with up to 93% yield and 99% ee. The control experiment and metal complex L1–Ni crystal supported the dual activation manner, in which the tridentate Bpy/Phen-BPI ligand contained two nitrogen atoms of the pyridine unit and one tertiary amine group of the pyrroloimidazolone moiety coordinating with Ni(II) to activate the 2-enoylpyridine-1-oxides, and the tertiary amine group of the additional pyrroloimidazolone moiety as the H-bond acceptor activated the indoles through a NH-bonding interaction, resulting in the asymmetric transformation. This represented the first example showing that the Bpy/Phen ligand contained three nitrogen atoms coordinating with the metal, and the additional nitrogen atom acted as the H-bond acceptor.

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手性模块化双功能c2对称联吡啶/邻菲罗啉-联吡罗咪唑酮配体的发展及其在非共价相互作用辅助对映选择性催化中的应用
手性联吡啶/菲罗啉配体因其丰富的配位化学性质而成为一类独特的配体。本文合成了13个新的c2对称手性菲罗啉-联吡咯咪唑酮配体(pheni - bpi)和5个新的c2对称手性联吡啶-联吡咯咪唑酮配体(BPy-BPI)。这些Bpy/ pheni - bpi螯合配体成功地进行了镍催化的吲哚与2-烯基吡啶-1-氧化物的不对称Friedel-Crafts烷基化反应,手性产物收率高达93%,ee高达99%。对照实验和金属配合物L1-Ni晶体支持双活化方式,其中三齿体Bpy/ pheni - bpi配体含有两个吡啶单元氮原子和一个吡咯咪唑酮部分叔胺基与Ni(II)配合活化2-烯基吡啶-1-氧化物,附加的吡咯咪唑酮部分叔胺基作为h键受体通过nh键相互作用活化吲哚。导致了不对称变换。这是第一个表明Bpy/Phen配体包含三个氮原子与金属配位,并且附加的氮原子充当氢键受体的例子。
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来源期刊
New Journal of Chemistry
New Journal of Chemistry 化学-化学综合
CiteScore
5.30
自引率
6.10%
发文量
1832
审稿时长
2 months
期刊介绍: A journal for new directions in chemistry
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