Origin of ligand-controlled regioselectivity in Co-catalyzed borylation of fluorinated arenes

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-07-28 DOI:10.1039/d5qo00897b

Xiaofang Zhai, Han Gao, Feng Ye, Wujie Wang, Yuliang Li, Gang Lu

引用次数: 0

Abstract

The mechanism and origins of regioselectivity in cobalt-catalyzed borylation of fluorinated arenes were computationally investigated. The results reveal that cobalt catalysts bearing two distinct pincer ligands exhibit different regioselectivity-determining steps. The ortho-selective borylation observed with the (PNP)Co catalyst is attributed to stronger electronic interactions in the σ-bond metathesis transition state. In contrast, the meta-selective borylation favored by the (CNC)Co catalyst arises from weaker electrostatic repulsion and enhanced charge transfer effects in the C–H oxidative addition transition state.

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氟化芳烃共催化硼化反应中配体控制区域选择性的来源

计算研究了钴催化氟化芳烃硼化反应中区域选择性的机理和来源。结果表明，携带两种不同钳形配体的钴催化剂表现出不同的区域选择性决定步骤。在（PNP）Co催化剂上观察到的邻选择性硼化反应是由于在σ键转化过渡态中有更强的电子相互作用。相比之下，（CNC）Co催化剂偏爱的亚选择性硼化反应是由于C-H氧化加成过渡态的静电斥力减弱和电荷转移效应增强所致。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.