Iron-Catalyzed Reactions in Organic Synthesis

Bolm, Carsten; Legros, Julien; Paih, Jacques Le; Zani, Lorenzo

doi:10.1021/cr040664h

Cited by 2,059 publications

(811 citation statements)

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“…Iron catalyzed-ATRP can be performed using low amounts of catalyst, reducing the toxicological risks as iron is considered less toxic and more environmentally friendly than copper [63][64][65]. Iron is also the most abundant metal on earth making it relatively cheap; these characteristics have initiated a lot of research and interest in Fe catalyzed organic chemistry, including ATRP, in line with the perspectives of "green chemistry" [66,67]. The choice of the ligand is a complex question; it depends on the nature of the polymer and the catalyst used [68]: for example, pentamethyldiethylenetriamine (PMDETA) can be used in combination with Cu [69], and tris(3,6-dioxaheptyl) amine (TDA) with Fe [70].…”

Section: Grafting Techniques 321 Atom Transfer Radical Polymerizatmentioning

confidence: 99%

PNIPAM grafted surfaces through ATRP and RAFT polymerization: Chemistry and bioadhesion

Conzatti

Cavalié

Combes

et al. 2017

Colloids and Surfaces B: Biointerfaces

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a b s t r a c tBiomaterials surface design is critical for the control of materials and biological system interactions. Being regulated by a layer of molecular dimensions, bioadhesion could be effectively tailored by polymer surface grafting. Basically, this surface modification can be controlled by radical polymerization, which is a useful tool for this purpose. The aim of this review is to provide a comprehensive overview of the role of surface characteristics on bioadhesion properties. We place a particular focus on biomaterials functionalized with a brush surface, on presentation of grafting techniques for "grafting to" and "grafting from" strategies and on brush characterization methods. Since atom transfer radical polymerization (ATRP) and reversible addition-fragmentation chain transfer (RAFT) polymerization are the most frequently used grafting techniques, their main characteristics will be explained. Through the example of poly(N-isopropylacrylamide) (PNIPAM) which is a widely used polymer allowing tuneable cell adhesion, smart surfaces involving PNIPAM will be presented with their main modern applications.

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Section: Grafting Techniques 321 Atom Transfer Radical Polymerizatmentioning

confidence: 99%

PNIPAM grafted surfaces through ATRP and RAFT polymerization: Chemistry and bioadhesion

Conzatti

Cavalié

Combes

et al. 2017

Colloids and Surfaces B: Biointerfaces

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“…21,22 Evidence for this came from the observation that complexes 4 and 6 give very similar conversions of ketones to hydrogenation products under the same conditions. Should this be the case, then the mechanism may resemble that commonly associated with the closely-related ruthenium 5 complexes (Figure 2), 16 in which hydrogen is transferred to substrate through a concerted, 6-membered ring mechanism, the well-defined nature of which contributes to the high level of enantiocontrol in the reduction. The enantiomerically-pure complexes 7 and 8 were prepared and characterised by X-ray crystallography, which revealed that the substituents on the bridging ethylene group were 15 axially positioned, possibly to avoid unfavourable steric clashes.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, significant breakthroughs have been made in 10 the development and applications of homogeneous iron-based catalysts to asymmetric transformations. [1][2][3][4][5][6][7][8][9][10][11] Several excellent reviews have been published which describe the key findings and many of the non asymmetric precedents for the catalysts in this review. Here the focus will be on recent developments 15 in asymmetric reactions, although some non-asymmetric reactions will be discussed where they serve to place new findings into context.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric catalysis using iron complexes – ‘Ruthenium Lite’?

Darwish

Wills

2012

Catal. Sci. Technol.

170

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“…However, in the last years Fe-catalyzed C-C bond cross coupling reactions of vinylic substrates and Grignard reagents became a subject of intense interest. [45][46][47][48][49][50][51] The vinylic counterpart is quite broad in scope, since vinylic halides, triflates, sulfonates, tosylates and enol phosphates can be used. [45][46][47][48][49][50][51] In continuation to our interest on the synthesis and synthetic applications of vinylic chalcogenides [52][53][54][55][56][57][58] we decided to study the feasibility of their use in cross coupling reaction with Grignard species catalyzed by iron.…”

Section: Introductionmentioning

confidence: 99%

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

Silveira¹,

Mendes²,

Wolf³

2010

J. Braz. Chem. Soc.

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Este trabalho descreve um novo método para a reação de acoplamento entre selenetos e teluretos vinílicos e reagentes de Grignard, catalisada por Fe(acac) 3 e à temperatura ambiente. A reação ocorre com retenção da configuração, fornecendo os respectivos alquenos em bons a excelentes rendimentos. Este método também é eficiente para a reação de acoplamento de calcogenetos bisvinílicos com reagentes de Grignard.A general new method for the cross-coupling reaction between vinylic selenides and tellurides and Grignard reagents catalyzed by Fe(acac) 3 at room temperature is described. This reaction proceeded with retention of configuration, providing the respective alkenes in good to excellent yields. This method is also efficient for the coupling reaction of divinyl chalcogenides with Grignard reagents. Keywords: iron-catalyzed, vinylic chalcogenides, cross-coupling, Grignard reagents IntroductionOrganochalcogenium compounds became the key component of a variety of versatile and useful reagents for organic synthesis. The multiple applications of organochalcogenium chemistry have been well described in a number of review articles 1-6 and books. 7-11 Functionalized alkynyl 12-18 and alkenyl [19][20][21][22][23] chalcogenides have a great potential in organic synthesis, since they are valuable intermediates for the selective preparation of several organic compounds.Among the many applications of vinylic selenides, divinylic selenides and vinylic sulfides, the cross-coupling reaction with Grignard reagents catalyzed by Ni 18,24-27 and Pd 28,29 to give the corresponding cross-coupled products, has been described. On the other hand, Pd 19,30 and Ni 24,[31][32][33] catalyzed cross coupling reactions and tellurium/metal exchange reactions [34][35][36][37][38][39][40][41][42] are demonstrative of the usefulness of vinylic tellurides.Transition-metal-catalyzed C-C bond coupling reactions are very important in many areas of science. 43,44 Most current methods require expensive transitionmetal catalysts and ligands. However, in the last years Fe-catalyzed C-C bond cross coupling reactions of vinylic substrates and Grignard reagents became a subject of intense interest. [45][46][47][48][49][50][51] The vinylic counterpart is quite broad in scope, since vinylic halides, triflates, sulfonates, tosylates and enol phosphates can be used. [45][46][47][48][49][50][51] In continuation to our interest on the synthesis and synthetic applications of vinylic chalcogenides 52-58 we decided to study the feasibility of their use in cross coupling reaction with Grignard species catalyzed by iron. To the best of our knowledge, iron catalysts have never been used for the coupling of vinylic selenides and tellurides as electrophiles. The possible use of iron catalysts would represent a great improvement over the high cost of palladium precursors and from the concerns about the toxicity of nickel salts. In light of the above comments it is of interest to design a simple, efficient, and versatile method for the stereoselective coupling of vinylic se...

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Iron-Catalyzed Reactions in Organic Synthesis

Cited by 2,059 publications

References 404 publications

PNIPAM grafted surfaces through ATRP and RAFT polymerization: Chemistry and bioadhesion

PNIPAM grafted surfaces through ATRP and RAFT polymerization: Chemistry and bioadhesion

Asymmetric catalysis using iron complexes – ‘Ruthenium Lite’?

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

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