铁催化芳基格氏试剂的联芳交叉偶联的反应机理

引用本文: 任清华, 沈晓燕. 铁催化芳基格氏试剂的联芳交叉偶联的反应机理[J]. 物理化学学报, 2015, 31(5): 852-858. doi: 10.3866/PKU.WHXB201503026 shu

Citation: REN Qing-Hua, SHEN Xiao-Yan. Reaction Mechanism for the Iron-Catalyzed Biaryl Cross-Coupling of Aryl Grignard Reagents[J]. Acta Physico-Chimica Sinica, 2015, 31(5): 852-858. doi: 10.3866/PKU.WHXB201503026 shu

铁催化芳基格氏试剂的联芳交叉偶联的反应机理

任清华 ,
沈晓燕

基金项目:
上海大学高性能计算平台"

自强4000"

与上海市高等教育内涵建设"

工程"

材料基因工程"

项目(B.58-B111-12-101, B.58-B111-12-103)资助 (B.58-B111-12-101, B.58-B111-12-103)

摘要:

利用密度泛函理论(DFT)计算研究了[Fe(MgBr)₂]催化的邻氯苯乙稀与溴代苯基镁反应生成联芳化合物的交叉偶联反应的机理. 研究了两个机理. 机理A包括三个基本步骤: (I) 氧化[Fe(MgBr)₂]生成[Ar-Fe(MgBr)],(II) 加成产生[Ar-(phenyl)-Fe(MgBr)₂], (III) 还原消除回到[Fe(MgBr)₂]. 机理B不形成[Ar-Fe(MgBr)]. 在第一步,溴代苯基镁在[Cl-Mg-Br]离解形成[Ar-Fe(MgBr)]之前直接进攻氧化加成后的中间体. 考虑溶剂效应后, 机理B优于机理A. 无论机理A还是机理B, 整个催化循环过程的决速步骤都是[Ar-(phenyl)-Fe(MgBr)₂]的还原消除再生催化剂[Fe(MgBr)₂]的步骤, 使用导体极化连续模型(CPCM)方法计算其在四氢呋喃溶剂中的吉布斯自由能(ΔG_sol)是82.98 kJ·mol^-1.

关键词:

English

Reaction Mechanism for the Iron-Catalyzed Biaryl Cross-Coupling of Aryl Grignard Reagents

1.
Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, P. R. China
Received Date: 25 December 2014
Available Online: 08 May 2015
Fund Project:
上海大学高性能计算平台"

自强4000"

与上海市高等教育内涵建设"

工程"

材料基因工程"

项目(B.58-B111-12-101, B.58-B111-12-103)资助

Abstract:

Mechanisms for the [Fe(MgBr)₂] catalyzed cross-coupling reaction between ortho-chlorostyrene and phenylmagnesium bromide to form biaryl were studied using density functional theory (DFT) calculations. We investigated two mechanisms. Cycle A included three basic steps: (I) oxidation of [Fe(MgBr)₂] to obtain [Ar- Fe(MgBr)], (II) addition to yield [Ar-(phenyl)-Fe(MgBr)₂], and (III) reductive elimination to return to [Fe(MgBr)₂]. Cycle B did not form [Ar-Fe(MgBr)]. In the first step, phenylmagnesium bromide attacks the intermediate of the oxidative addition directly before [Cl-Mg-Br] dissociates to form [Ar-Fe(MgBr)]. The catalytic Cycle B is favored over the catalytic Cycle Awhen considering the solvent effect. The rate-limiting step in the overall catalytic cycle for both Cycle A and Cycle B is the reductive elimination of [Ar-(phenyl)-Fe(MgBr)₂] to regenerate the catalyst [Fe(MgBr)₂], where the Gibbs free energy in solvent tetrahydrofuran (THF), ΔG_sol, is 82.98 kJ ·mol^-1, as determined using the conductor polarized continuum model (CPCM) method.

Key words:

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沈阳化工大学材料科学与工程学院沈阳 110142

铁催化芳基格氏试剂的联芳交叉偶联的反应机理

English

Reaction Mechanism for the Iron-Catalyzed Biaryl Cross-Coupling of Aryl Grignard Reagents

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

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CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

铁催化芳基格氏试剂的联芳交叉偶联的反应机理

English

Reaction Mechanism for the Iron-Catalyzed Biaryl Cross-Coupling of Aryl Grignard Reagents

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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