Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

Jana, Ranjan; Pathak, Tejas P.; Sigman, Matthew S.

doi:10.1021/cr100327p

Cited by 2,026 publications

(863 citation statements)

References 532 publications

(1,280 reference statements)

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“…6 Recent worldwide interest in practical research applications, based on the utilization of abundant earth elements and the practical advantages of iron catalysts, including low cost, low toxicity, high availability, and easy separation of metal residues, have also demanded a much greater focus on iron-catalyzed cross-coupling reactions.…”

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confidence: 99%

Investigation of Organoiron Catalysis in Kumada–Tamao–Corriu-Type Cross-Coupling Reaction Assisted by Solution-Phase X-ray Absorption Spectroscopy

Takaya

Nakajima

Nakagawa

et al. 2015

Bulletin of the Chemical Society of Japan

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Solution-phase synchrotron X-ray absorption spectroscopy (XAS) is a powerful tool for structural and mechanistic investigations of paramagnetic organoiron intermediates in solution-phase reactions. For paramagnetic organotransition metal intermediates, difficulties are often encountered with conventional NMR-and EPR-based analyses. By using solution-phase XAS, we succeeded in identifying the organoiron species formed in the reaction of iron bisphosphine with mesitylmagnesium bromide, MesMgBr, and 1-bromodecane in a [FeX 2 (SciOPP)]-catalyzed KumadaTamaoCorriu (KTC)-type cross-coupling reaction. X-ray absorption near-edge structure (XANES) spectra showed that the resulting aryliron species possessed a divalent oxidation state. Extended X-ray absorption fine structure (EXAFS) demonstrated that the solution-phase molecular geometries of these species are in satisfactory agreement with the crystallographic geometries of [Fe The renaissance of iron-catalyzed cross-coupling reactions in the last decade 15 has been triggered by their unprecedented nonclassical reactivities and selectivities in comparison with conventional Pd and Ni catalysts.6 Recent worldwide interest in practical research applications, based on the utilization of abundant earth elements and the practical advantages of iron catalysts, including low cost, low toxicity, high availability, and easy separation of metal residues, have also demanded a much greater focus on iron-catalyzed cross-coupling reactions.

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confidence: 99%

Investigation of Organoiron Catalysis in Kumada–Tamao–Corriu-Type Cross-Coupling Reaction Assisted by Solution-Phase X-ray Absorption Spectroscopy

Takaya

Nakajima

Nakagawa

et al. 2015

Bulletin of the Chemical Society of Japan

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“…Essas reações são muito importantes em síntese orgânica, sendo consideradas como uma das melhores abordagens em termos de formação de novas ligações C-C (Csp . [35][36][37][38][39][40] O reconhecimento da importância desse método foi dada pela concessão do Prêmio Nobel de 2010, outorgado aos pesquisadores japoneses Ei-ichi Negishi e Akira Suzuki e ao americano Richard Heck.…”

Section: Reações De Acoplamento Cruzadounclassified

An Overview of the Different Types of Catalysts in Organic Synthesis

Dias¹,

Ferreira²,

Cunha³

2012

Revista Virtual De Química

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Abstract:Since the mid-twentieth century, by economic and environmental factors, many researchers and some industries are investing in the development of syntheses and technologies that are environmentally friendly, producing less toxic waste and saving energy. Furthermore, the use of renewable raw materials, biomass and the development of asymmetric methods that provide products with high yields and selectivities becomes a major challenge for researchers in various fields that employ the catalytic process. This paper describes the importance of catalysis in organic synthesis of complex molecules, especially for the pharmaceutical and fine chemicals industries. Indeed, the industrial revolution caused by catalysis in different sectors such as petrochemicals, plastics, paper, among others, also became the subject of interest of this review.Keywords: Homogeneous catalysis; heterogeneous catalysis; biocatalysis; organocatalysis. ResumoDesde meados do século XX, por razões econômicas e ambientais, diversos pesquisadores e algumas indústrias investem no desenvolvimento de tecnologias sintéticas que sejam ambientalmente favoráveis, gerando menos resíduos tóxicos e com economia de energia. Além disso, os processos catalíticos e biocatalíticos associados ao uso de biomassas renováveis são de fundamental importância para a produção de matérias-primas quirais e aquirais com altos rendimentos e elevadas seletividades. Esse conjunto de paradigmas é um dos grandes desafios da atualidade para os pesquisadores nos diversos ramos da síntese orgânica.Este trabalho descreve a importância da catálise e da biocatálise na síntese orgânica de moléculas complexas, destacando-se os setores de química fina e fármacos. Além disso, a utilização crescente dos diversos processos catalíticos em diferentes setores industriais, tais como petroquímico, de papel e celulose, plásticos, e muitos outros também são assuntos de interesse desse trabalho de revisão.Palavras-chave: Catálise homogênea; catálise heterogênea; biocatálise; organocatálise.

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“…Some important reactions in this context, which are widely applied in organic synthesis, can be mentioned, such as the Suzuki-Miyaura, Stille, Negishi, Sonogashira, Mizoroki-Heck and BuchwaldHartwig couplings. [16][17][18] Because of the characteristic insolubility of cellulose and some of its derivatives, a plenty of studies has been carried using those material as heterogeneous support in SuzukiMiyaura coupling reactions. Palladium nanoparticles have been supported on cellulose without modification and applied to Suzuki-Miyaura couplings.…”

Section: Introductionmentioning

confidence: 99%

Cellulose Oxidation and the Use of Carboxyl Cellulose Metal Complexes in Heterogeneous Catalytic Systems to Promote Suzuki-Miyaura Coupling and C−O Bond Formation Reaction

Martins

Santos

Rodrigues

et al. 2017

J. Braz. Chem. Soc.

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This work shows the modification of microcrystalline cellulose by the selective oxidation of primary hydroxyl groups to carboxylate groups by a 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)-mediated system and its application as a heterogeneous ligand by ionic exchange with catalytic metals ions such as palladium, nickel and copper. Afterwards is described the application of the synthesized material as catalyst in coupling reactions such as Suzuki-Miyaura coupling and C−O bond formation reaction in different conditions, which are of great importance for the synthesis of drugs, natural products and new materials such as dendrimers, liquid crystals and polymers with magnetic and optical properties. The carboxyl cellulose matrix shows to have superior catalytic results as a ligand for all coupling reactions. Can be also highlighted the affinity of the carboxyl cellulose ligand in polar solvents such as water and alcohols and its application in mild conditions.

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Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

Cited by 2,026 publications

References 532 publications

Investigation of Organoiron Catalysis in Kumada–Tamao–Corriu-Type Cross-Coupling Reaction Assisted by Solution-Phase X-ray Absorption Spectroscopy

Investigation of Organoiron Catalysis in Kumada–Tamao–Corriu-Type Cross-Coupling Reaction Assisted by Solution-Phase X-ray Absorption Spectroscopy

An Overview of the Different Types of Catalysts in Organic Synthesis

Cellulose Oxidation and the Use of Carboxyl Cellulose Metal Complexes in Heterogeneous Catalytic Systems to Promote Suzuki-Miyaura Coupling and C−O Bond Formation Reaction

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