Iron‐Catalyzed Cross‐Coupling Reaction of Vinyl Bromides or Chlorides with Imidazoles in the Absence of Ligands and Additives

Mao, Jincheng; Xie, Guanlei; Zhan, Jiaming; Hua, Qiongqiong; Shi, Daqing

doi:10.1002/adsc.200900066

Cited by 40 publications

(11 citation statements)

References 35 publications

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“…Hence, we designed a coupling reaction between the 2‐position of imidazole or benzimidazole and a benzene ring. We chose the ( Z )‐1‐styryl‐1 H ‐imidazole ( 3a ) as the starting material, which could be prepared easily via the cross‐coupling of ( Z )‐2‐bromovinylbenzene with imidazole catalyzed by Fe(III) (Scheme ) 14…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Oxidative Intramolecular CC Bond Formation via Double sp² CH Activation between the 2‐Position of Imidazoles and a Benzene Ring

Sun

Zheng

et al. 2012

Adv Synth Catal

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Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Oxidative Intramolecular CC Bond Formation via Double sp² CH Activation between the 2‐Position of Imidazoles and a Benzene Ring

Sun

Zheng

et al. 2012

Adv Synth Catal

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“…Later, the iron-catalyzed amination of alkenyl bromides/chlorides without the use of ligands and additives was reported by Mao (Scheme 4b). [18] Interestingly, the coupling reaction of (E)-vinyl bromides mainly produced (Z)-products, while the use of (E)vinyl chlorides as substrates predominantly led to (E)-isomers. These results might be due to the effect of substituents and leaving groups on the alkenyl halides.…”

Section: Iron-catalyzed Csp 2 -N Bond Formationmentioning

confidence: 99%

Iron‐Catalyzed Cross‐Coupling Reactions for the Construction of Carbon‐Heteroatom Bonds

et al. 2020

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Carbon-heteroatom bonds are ubiquitous among pesticides, pharmaceutical agents, and natural products. In recent years, significant progress has been made in transition-metal-catalyzed carbon-heteroatom bond formation. Especially, iron-catalyzed reactions have become a focused area in organic chemistry owing to their advantages of low cost, economical and environmental benignity. This review intends to summarize the recent advances in the construction of carbon-heteroatom bonds via cross-coupling reactions using iron as a catalyst, including the formation of CÀ N, CÀ O, CÀ S, CÀ B, and CÀ Si bonds. A series of nucleophilic heteroatoms reagents, reaction classifications, and iron catalytic systems are discussed. In addition, some mechanistic studies have also been described. formation of CÀ N, CÀ O, CÀ S, CÀ B, and CÀ Si bonds are mainly focused. 2. Iron-Catalyzed CÀ N Bond Formation The construction of CÀ N bond by transition metal-catalyzed is one of the most significant transformations in organic synthesis, which is widely employed in chemical, pharmaceutical, and materials industries. [8] The classical method to access CÀ N bond is through the transition metal-catalyzed cross-coupling reaction between aryl or alkenyl halides and amines, also known as Buchwald-Hartwig amination reaction. In recent years, the formation of CÀ N bond via CÀ H activation has been welldocumented. [9] After decades of development, the great progress has been achieved in the transition metals (Cu, Pd, Ni, Fe, Co) catalyzed the construction of the CÀ N bond. [10] However, compared with other transition metals, iron-catalyzed CÀ N bond formation has less been studied, which might be caused by the negative effect of trace metals. [21-22] 2.1. Iron-Catalyzed CspÀ N Bond Formation Alkynamines are essential compounds, widely used in organic reactions such as pericyclic reaction, tandem RCM, Pauson-Khand reaction, Kinugasa reaction, Saucy-Marbet rearrangement, and Ficini-Claisen rearrangement. [11] In 2009, Zhang and coworkers [11e] developed the first example of iron-catalyzed amination of alkynyl bromides (Scheme 1). Nucleophiles such as amide, sulfonamide, and indole could react with alkynyl bromides to obtain alkynamines in high yields under FeCl 3 * 6H 2 O and DMEDA catalytic system. This reaction exhibits good functional group tolerance, and the functional groups

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“…6,164.4,137.9,133.6,132.2,129.7,129.5,129.0,127.4,124.1,110.9;HRMS (ESI) 164.5, 163.9, 140.4, 139.0, 132.1, 131.7, 129.8, 129.1, 127.5, 127.0, 123.9, 109.0, 21.5 …”

Section: 反式-2-(4-氯苯乙烯基mentioning

confidence: 99%

Alkenylation of Heterocycle C—H Catalyzed by CuI Nanoparticles

Gui-de¹,

Wang²,

Zhang³

et al. 2015

Chin. J. Org. Chem.

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The heterocycles and their derivatives are important organic compounds which are widely existed in various natural products and synthetic compounds. Alkenylated heterocycles have great value in the synthesis of natural products, medicine molecules, photoelectric materials and high active polymers. Herein, an efficient method was developed for C-H functionalization of heterocycles to synthesize alkenylated heterocycles with CuI nanoparticles as catalyst, K 3 PO 4 as base, 1,10-phenanthroline as ligand, diglyme as solvent under reflux in argon atmosphere for 24 h. The CuI nanoparticles can be recycled and reused without any significant decrease in catalytic activity. In addition, various aromatic heterocycles can be applied to our catalytic system, and acidity of heterocycle C-H bonds is critical to the reactivity. 18 corresponding trans-alkenylated heterocycles were obtained and characterized.

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Iron‐Catalyzed Cross‐Coupling Reaction of Vinyl Bromides or Chlorides with Imidazoles in the Absence of Ligands and Additives

Cited by 40 publications

References 35 publications

Palladium‐Catalyzed Oxidative Intramolecular CC Bond Formation via Double sp² CH Activation between the 2‐Position of Imidazoles and a Benzene Ring

Palladium‐Catalyzed Oxidative Intramolecular CC Bond Formation via Double sp² CH Activation between the 2‐Position of Imidazoles and a Benzene Ring

Iron‐Catalyzed Cross‐Coupling Reactions for the Construction of Carbon‐Heteroatom Bonds

Alkenylation of Heterocycle C—H Catalyzed by CuI Nanoparticles

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Iron‐Catalyzed Cross‐Coupling Reaction of Vinyl Bromides or Chlorides with Imidazoles in the Absence of Ligands and Additives

Cited by 40 publications

References 35 publications

Palladium‐Catalyzed Oxidative Intramolecular CC Bond Formation via Double sp2 CH Activation between the 2‐Position of Imidazoles and a Benzene Ring

Palladium‐Catalyzed Oxidative Intramolecular CC Bond Formation via Double sp2 CH Activation between the 2‐Position of Imidazoles and a Benzene Ring

Iron‐Catalyzed Cross‐Coupling Reactions for the Construction of Carbon‐Heteroatom Bonds

Alkenylation of Heterocycle C—H Catalyzed by CuI Nanoparticles

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Product

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Palladium‐Catalyzed Oxidative Intramolecular CC Bond Formation via Double sp² CH Activation between the 2‐Position of Imidazoles and a Benzene Ring

Palladium‐Catalyzed Oxidative Intramolecular CC Bond Formation via Double sp² CH Activation between the 2‐Position of Imidazoles and a Benzene Ring