Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis: The Formation of Carbon-Carbon Bonds

Iqbal, Javed; Bhatia, Beena; Nayyar, N. K.

doi:10.1021/cr00026a008

Cited by 680 publications

(250 citation statements)

References 54 publications

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“…Various metal (ruthenium, iron, copper) complexes eff ective for ATRA 19 and metal-catalysed living radical polymerization or atom-transfer radical polymerization 24 -28 were then used for the step-growth radical polymerization of these abc monomers. Th e vinyl group and the C -Cl bond of the monomers were consumed with all the metal catalysts, although the rates and molecular weights of the products were dependent on both catalysts and monomers ( Supplementary Figs.…”

Section: Abc Monomersmentioning

confidence: 99%

“…1c ). We have recently developed the metal-catalysed radical polyaddition by evolution of metal-catalysed atom-transfer radical addition (ATRA) or Kharasch addition 19 into the step-growth polymerization of a designed monomer possessing an unconjugated C = C double bond and a reactive C -Cl bond 20,21 . Th is polymerization proceeds through a C -C bond forming reactions between the radical species generated through the metal-catalysed activation of the C -Cl bond and the unconjugated C = C bond of another molecule to lead to linear polymers by step-growth propagation.…”

mentioning

confidence: 99%

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Sequence-regulated vinyl copolymers by metal-catalysed step-growth radical polymerization

et al. 2010

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Proteins and nucleic acids are sequence-regulated macromolecules with various properties originating from their perfectly sequenced primary structures. However, the sequence regulation of synthetic polymers, particularly vinyl polymers, has not been achieved and is one of the ultimate goals in polymer chemistry. In this study, we report a strategy to obtain sequenceregulated vinyl copolymers consisting of styrene, acrylate and vinyl chloride units using metalcatalysed step-growth radical polyaddition of designed monomers prepared from common vinyl monomer building blocks. Unprecedented ABCC-sequence-regulated copolymers with perfect vinyl chloride -styrene -acrylate -acrylate sequences were obtained by copper-catalysed step-growth radical polymerization of designed monomers possessing unconjugated C = C and reactive C -Cl bonds. This strategy may open a new route in the study of sequence-regulated synthetic polymers.

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Section: Abc Monomersmentioning

confidence: 99%

mentioning

confidence: 99%

Sequence-regulated vinyl copolymers by metal-catalysed step-growth radical polymerization

et al. 2010

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“…Catalytic functionalization is a well-established process in organic synthesis and an efficient method for the preparation of high added value products [5][6][7][8], among which is catalyzed Kharasch addition or atom transfer radical addition (TMC ATRA) which is an effective tool for carbon-carbon bond formation and has gained considerable interest in organic synthesis during the last 50-60 years [9][10][11]. On the other hand, it is a synthetically useful process for functionalizing organic compounds by means of halogen derivatives with a high level of atom economy.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Synthesis and Antifungal Activity of New Polychlorinated Natural Terpenes

Ighachane

Boualy

Ali

et al. 2017

Advances in Materials Science and Engineering

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Various unsaturated natural terpenes were selectively converted to the corresponding polychlorinated products in good yields using iron acetylacetonate in combination with nucleophilic cocatalyst. The synthesized compounds were evaluated for their in vitro antifungal activity. The antifungal bioassays showed that 2c and 2d possessed significant antifungal activity against Fusarium oxysporum f. sp. albedinis (Foa), Fusarium oxysporum f. sp. canariensis (Foc), and Verticillium dahliae (Vd).

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“…It is well known that Mn(OAc) 3 1-14 and (NH 4 ) 2 Ce(NO 2 ) 6 (CAN) [15][16][17][18][19][20][21][22][23][24] are widely used as radical oxidants in the synthesis of poly functional organic compounds forming C-C bond between basic compounds. These radical oxidants enable formation of dihydrofurans obtained from reaction of 1,3-dicarbonyls, 3-oxopropanenitriles, β-ketoesters and their derivatives with alkenes easily prepared by basic methods.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-(2-phenylethenyl) substituted 4,5-dihydrofurans by regioselective addition of 1,3-dicarbonyl compounds to dienes promoted by cerium(IV) ammonium nitrate

Yılmaz

Ustalar²

2016

Arkivoc

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Radical addition of 1,3-dicarbonyl compounds to conjugated dienes in the presence of cerium(IV) ammonium nitrate in THF produced 4,5-dihydrofurans in good to excellent yields. All radical additions occurred on the terminal double bond as regioselective. Two different dihydrofurans were obtained from the reaction of 1-phenyl-1,3-butanedione with 1-phenyl-1,3-butadiene and 3-methyl-1-phenyl-1,3-butadiene. All compounds were characterised by IR, 1 H, 13 C-NMR and HRMS spectra.

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Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis: The Formation of Carbon-Carbon Bonds

Cited by 680 publications

References 54 publications

Sequence-regulated vinyl copolymers by metal-catalysed step-growth radical polymerization

Sequence-regulated vinyl copolymers by metal-catalysed step-growth radical polymerization

Catalytic Synthesis and Antifungal Activity of New Polychlorinated Natural Terpenes

Synthesis of 2-(2-phenylethenyl) substituted 4,5-dihydrofurans by regioselective addition of 1,3-dicarbonyl compounds to dienes promoted by cerium(IV) ammonium nitrate

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