Novel Synthetic Method of Phenol from Benzene Catalysed by Perfluorinated Hemin

Tsuchiya, Soji; Senō, Manabu

doi:10.1246/cl.1989.263

Cited by 90 publications

(47 citation statements)

References 7 publications

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“…Fluorination reagents include N -fluoropyridinium triflates [69], cesium fluoroxysulfate [70], and fluorides of cobalt or silver [71]. N -Chlorosuccinimide (NCS) [72-77] or chlorine [64, 65] are normally used for chlorination, although HCl/H 2 O 2 [78] and PhSeCl 3 [79] have also been reported.…”

Section: Porphyrin Functionalizationmentioning

confidence: 99%

Syntheses and Functionalizations of Porphyrin Macrocycles

Vicente¹,

Smith²

2014

COS

110

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Porphyrin macrocycles have been the subject of intense study in the last century because they are widely distributed in nature, usually as metal complexes of either iron or magnesium. As such, they serve as the prosthetic groups in a wide variety of primary metabolites, such as hemoglobins, myoglobins, cytochromes, catalases, peroxidases, chlorophylls, and bacteriochlorophylls; these compounds have multiple applications in materials science, biology and medicine. This article describes current methodology for preparation of simple, symmetrical model porphyrins, as well as more complex protocols for preparation of unsymmetrically substituted porphyrin macrocycles similar to those found in nature. The basic chemical reactivity of porphyrins and metalloporphyrin is also described, including electrophilic and nucleophilic reactions, oxidations, reductions, and metal-mediated cross-coupling reactions. Using the synthetic approaches and reactivity profiles presented, eventually almost any substituted porphyrin system can be prepared for applications in a variety of areas, including in catalysis, electron transport, model biological systems and therapeutics.

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Section: Porphyrin Functionalizationmentioning

confidence: 99%

Syntheses and Functionalizations of Porphyrin Macrocycles

Vicente¹,

Smith²

2014

COS

110

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“…Numerous porphyrins with polyhalogen substituents at the periphery of the macrocycle have been reported in the literature [1]. The interests in this class of perhaloporphyrins are four fold: (1) synthetic utility [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21], (2) interesting physicochemical properties [10,, (3) robust catalysts for the oxidative transformation of organic substrates [6,[60][61][62][63][64][65][66][67][68][69][70][71][72], (4) useful precursors for the synthesis of a variety of other synthetically difficult or inaccessible porphyrins [73][74][75][76][77][78][79][80][81][82][83]…”

Section: Introductionmentioning

confidence: 99%

Highly brominated porphyrins: synthesis, structure and their properties

Bhyrappa

Bhavana

Vittal

2003

J. Porphyrins Phthalocyanines

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This article reports the first perbromination of β-pyrrole and meso-phenyl groups of the 5,10,15,20-tetrakis(3ʼ,5ʼ-dimethoxyphenyl)porphinato copper(II) to generate highly brominated porphyrin, 2, 3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(2ʼ,6ʼ-dibromo-3ʼ,5ʼ-dimethoxyphenyl)-porphinato copper(II), CuT(3ʼ,5ʼ-DMP)PBr 16 complex. Its crystal structure exhibited unusual five-coordination geometry with saddle shaped conformation of the porphyrin core. H 2 T(3ʼ,5ʼ-DMP)PBr 16 and its metal complexes exhibited large anodic shift of oxidation potentials with marginal changes in reduction potentials relative to their corresponding octabromotetraphenylporphyri n, MTPPBr 8 derivatives. The enhanced electron deficiency of the ZnT(3ʼ,5ʼ-DMP)PBr 16 complex was probed by axial ligation of various Lewis bases with differing pK a values. The ZnT(3ʼ,5ʼ-DMP)PBr 16 complex exhibited decrease in equilibrium constants for the ligation of bases relative to sterically unhindered ZnTPPBr 8 . This has been ascribed to the sterics induced by the bulky ortho-bromo phenyl substituents that prevents the facile binding of Lewis bases to the Zn(II)-center.

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“…Better yields of fluorinated 2 were obtained by using an excess of N-fluoropyridinium triflates in hexafluorobenzene [80]. In the presence of a metal fluoride (CoF 2 or AgF 2 ), under an inert atmosphere, a refluxing solution of the Zn(II) complex of meso-tetra-aryl porphyrin in CHCl 3 affords the octafluorinated derivative 86 [81]. achieved by using one equivalent of NCS or NBS, although dihalogenated products are also formed in lesser yield.…”

Section: Halogenationmentioning

confidence: 99%