The Origin of Enantioselectivity of Aryl Terminal Alkenes Hydroboration Catalyzed by Cobalt Complex: A Density Functional Theory (DFT) Study

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-04-08 DOI:10.1021/acs.orglett.5c00809

Xiaofan Shi, Ling Zhu, Lin Zhang, Zuoyin Yang, Min Pu, Ming Lei

引用次数: 0

Abstract

Density functional theory (DFT) studies reveal the origin of the regioselectivity and stereoselectivity in Co-IPO-catalyzed hydroboration of aryl alkenes. Four insertion pathways dictate selectivity, with anti-Markovnikov S-product formation (Path A) being energetically favored. The alkene insertion step and σ-bond metathesis step jointly determine the selectivity of the reaction. In addition, the steric hindrance from the −NPhⁱPr₂ moiety of the IPO ligand critically controls selectivity. Interestingly, substituting −NPhⁱPr₂ with −NCH₃ shifts selectivity toward Markovnikov products.

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钴配合物催化芳基端烯烃氢硼化对映选择性的起源：密度泛函理论（DFT）研究

密度泛函理论（DFT）研究揭示了co - ipo催化芳基烯烃硼化反应中区域选择性和立体选择性的来源。四种插入途径决定了选择性，反马尔可夫尼科夫s产物形成（路径A）在能量上更有利。烯烃插入步骤和σ键复合步骤共同决定了反应的选择性。此外，来自IPO配体- NPhiPr2部分的空间位阻对选择性有重要的控制作用。有趣的是，用- NCH3取代- NPhiPr2会使选择性转向马尔可夫尼科夫产物。

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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.