Cyanation of aromatic halides

Ellis, G. P.; Romney-Alexander, T. M.

doi:10.1021/cr00080a006

Cited by 551 publications

(234 citation statements)

References 22 publications

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“…Whilst a considerable number of methods for transition-metal mediated halogen-exchange have been reported, we are still far from developing methods for all the transformations I-IV 10 identifed above:…”

Section: Discussionmentioning

confidence: 99%

“…It is therefore of great importance to obtain an understanding of the many factors which affect the steps i-iii. The oxidative addition of all types of aryl halides and pseudo-halides to transition-metal complexes (i) 10 has been reported, and this process is generally well understood for metals such as palladium. Similarly, exchange of halide ligands at the metal centre has been used to synthesise a variety of complexes, and this process is generally considered to be rapid.…”

Section: Possible Mechanismsmentioning

confidence: 99%

“…Under these conditions, the 5 reaction is only prepartively useful for the preparation of chlorides (32c) from bromides (32b) or iodides (32a), and the preparation of bromides from iodides, neither of which are usually synthetically useful. An alternative procedure using copper(I) oxide as a catalyst in the presence of lithium, 10 sodium or quaternary ammonium halides was slightly more general, although only low conversions were obtained for reactions in the 'reverse' direction (E.g. a 7% yield of 32a was obtained from reaction of 32b with NaI).…”

Section: Possible Mechanismsmentioning

confidence: 99%

“…[56][57][58][59] There is very good evidence that the reactions in Scheme 17 proceed via a Palladium(II)/Palladium(IV) catalytic cycle. Thus, coordination of the directing group to the Pd(II) species facilitates C-H activation on the aromatic ring to give an 10 arylpalladium species (Scheme 18, 84). This is oxidised to a Pd(IV) complex 86 by the electrophilic halogenating agent 85, and then undergoes reductive elimination to give the aryl halide product 87 and regenerate a catalytically active Pd(II) species.…”

Section: Palladiummentioning

confidence: 99%

“…Fluorides are often particularly important but there are very few industrially viable methods for the introduction of fluorine atoms into an aromatic ring. Typically 10 aryl flourides are either bought in as starting materials, or the fluoride must be introduced via an S N Ar reaction or diazotisation chemistry. Sulphonate esters derived from phenols can be employed as alternatives to aryl halides in many cross-coupling reactions, and these are often referred to 15 as 'pseudo-halides'.…”

Section: Introductionmentioning

confidence: 99%

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Metal-catalysed halogen exchange reactions of aryl halides

Sheppard

2009

Org. Biomol. Chem.

125

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Aryl halides are common synthetic targets themselves, and also highly versatile synthetic intermediates. Aryl chlorides are much more widely available and easier to synthesise than the other halide derivatives, so the development of effective methods for interconverting aryl halide derivatives would therefore be extremely useful. This article outlines which transformations are particularly desirable, and describes the progress that has been made on developing methods for carrying out those transformations using copper, nickel or palladium catalysts. The possible mechanisms of these reactions are discussed, with a view to identifying areas for future investigation.

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Section: Discussionmentioning

confidence: 99%

Section: Possible Mechanismsmentioning

confidence: 99%

Section: Possible Mechanismsmentioning

confidence: 99%

Section: Palladiummentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Metal-catalysed halogen exchange reactions of aryl halides

Sheppard

2009

Org. Biomol. Chem.

125

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Oligo-2,6-naphthylenevinylenes – New Building Blocks for the Preparation of Photoluminescent Polymeric Materials

1999

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Synthetic strategies towards appropriate symmetric and unsymmetric functionalization of the naphthalene ring are presented. By means of Knoevenagel and Wittig condensation reactions new fluorescent, differently functionalized oligo(2,6‐naphthylenevinylene)s have been synthesized, the presence of terminal aldehyde or bromine substitution opening the way to the incorporation of the fluorescent trimers in a variety of polymeric materials. The effect of substituting the phenylene ring by the more bulky dialkoxynaphthalene system in arylenevinylene‐type materials is studied from the structural point of view and the possibility to tune the emission color and the electron affinity through the introduction of naphthylenevinylene and cyano‐substituted naphthylenevinylene units is also investigated.

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Synthesis of Novel Functionalised Zinc Phthalocyanines Applicable in Photodynamic Therapy

Drechsler

Pfaff

Hanack³

1999

Eur. J. Org. Chem.

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The synthesis of several new phthalonitriles 3, 9, 14, 25, 33, and 36, functionalised with carboxyl groups, including two examples of amino acid derivatives is described. All new phthalonitriles were converted into their corresponding phthalocyaninatozinc compounds. The phthalocyanines, 2,3,9,10,16,17,23,24‐octa(1‐carboxyethyloxy)phthalocyaninatozinc (5), 2,9,16,23‐tetra(2‐amino‐2‐carboxyethyl)phthalocyaninatozinc (11), 2,9,16,23‐tetra(1‐carboxy‐2‐hydroxyethylaminocarbonyl)phthalocyaninatozinc (16), 1,8,15,22‐tetra(carboxybutyl)phthalocyaninatozinc (27), 2,3,9,10,16,17,23,24‐octa(carboxyalkyl)phthalocyaninatozinc (39), and the nonidentically substituted 9,10,16,17,23,24‐hexa(carboxyalkyl)‐2‐[4‐(N‐succinimidyloxycarbonyl)butyl]phthaloyaninatozinc (41) are all sufficiently soluble in water. The nonidentically‐substituted compounds are important due to their selective binding to tumor‐selective antibodies. UV/Vis‐spectroscopy was used to investigate the effect of more or less sterically‐demanding substituents in the periphery of the phthalocyanines towards aggregation. The phototoxicity towards cancer cells of some of the new compounds was investigated in several in‐vitro experiments.

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Cyanation of aromatic halides

Cited by 551 publications

References 22 publications

Metal-catalysed halogen exchange reactions of aryl halides

Metal-catalysed halogen exchange reactions of aryl halides

Oligo-2,6-naphthylenevinylenes – New Building Blocks for the Preparation of Photoluminescent Polymeric Materials

Synthesis of Novel Functionalised Zinc Phthalocyanines Applicable in Photodynamic Therapy

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