n -9-花青素-吡啶- cu (OAc)2催化烷基烯二腈不对称直接卤化反应的齿轮效应

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-03 DOI:10.1021/acs.orglett.4c0340510.1021/acs.orglett.4c03405

Yuri Takagi, Takaaki Saito, Natsuki Mizuno and Takayoshi Arai*,

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引用次数: 0

摘要

新建立的n -9-蒽酰甲基双（咪唑烷）吡啶（n -9-花青素-吡啶）-Cu(OAc)2配合物催化烷基二腈与n -溴琥珀酰亚胺和n -氯琥珀酰亚胺的不对称卤代酰化反应，利用琥珀酰亚胺部分直接作为铜结合的亲核试剂。蒽基取代基表现出一种联动效应，使得配体中咪唑烷环的N-H质子形成了一个组织良好的非对称球体。配合效应使得氢键辅助铜催化的卤化反应具有较高的对映选择性。

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Gearing Effects on N-9-Anth-PyBidine-Cu(OAc)2-Catalyzed Asymmetric Direct Haloimidation Reactions of Alkylidenemalononitriles

A newly developed N-9-anthranylmethyl bis(imidazolidine)pyridine (N-9-Anth-PyBidine)-Cu(OAc)₂ complex catalyzed asymmetric haloimidation reactions of alkylidenemalononitriles with N-bromosuccinimide and N-chlorosuccinimide, employing the succinimide moiety directly as a copper-bound nucleophile. The anthranyl substituent showed a gearing effect that produced a well-organized asymmetric sphere involving the N-H proton of the imidazolidine ring in the ligand. The gearing effect afforded hydrogen bonding-assisted copper-catalyzed haloimidation reactions with high enantioselectivity.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.