2.2.3 Cyanation of Aryl Halides

A. Ouali; M. Taillefer

doi:10.1055/sos-SD-213-00055

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van Leeuwen, P. W. N. M.: 2014 Science of Synthesis, 2013/8: C-1 Building Blocks in Organic Synthesis 2 DOI: 10.1055/sos-SD-213-00055

C-1 Building Blocks in Organic Synthesis 2

2.2.3 Cyanation of Aryl Halides

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Herausgeber: van Leeuwen, P. W. N. M.

Autoren: Ballini, R.; Belderrain, T. R.; Bruneau, C.; Cokoja, M.; Dong, D.; Fischmeister, C.; Grushin, V. V.; Hu, J.; Ibrahim, H.; Iwasawa, N.; Kaposi, M.; Kühn, F. E.; Lishchynskyi, A.; Merino, P.; Molander, G. A.; Müller, C.; MuÇoz-Molina, J. M.; Neumann, H.; Ni, C.; Nicasio, M. C.; Novák, P.; Nozaki, K.; Ouali, A.; Petrini, M.; Rutjes, F. P. J. T.; Ryu, D.; Schoonen, L.; Schranck, J.; Taillefer, M.; Takahashi, K.; Takaya, J.; te Grotenhuis, C.; Witt, J.; Zhang, N.

Titel: C-1 Building Blocks in Organic Synthesis 2

Untertitel: Alkenations, Cross Couplings, Insertions, Substitutions, and Halomethylations

Print ISBN: 9783131751218; Online ISBN: 9783132064515; Buch-DOI: 10.1055/b-003-125817

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: C1-bildende Blöcke in der organischen Synthese

Science of Synthesis Reference Libraries

Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Typ: Mehrbändiges Werk

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Abstract

The cyanation of aryl halides (iodides, bromides, and chlorides) constitutes a very useful transformation in organic chemistry. Indeed, it allows the preparation of arenecarbonitriles, which are important intermediates and targets throughout life and material sciences. The most convenient methods for the cyanation of aryl halides (Ar¹X) involve a transition-metal catalyst and a cyanide source, the most common ones being alkali metal cyanides, zinc cyanide, potassium hexacyanoferrate(II), and, to a lesser extent, cyanohydrins or trimethylsilyl cyanide. The main transition metals able to promote such reactions are nickel, palladium, and copper. The choice of the metal mainly depends on the nature of the aryl halide to be converted, with the reactivity of aryl halides decreasing from aryl iodides to aryl bromides to aryl chlorides. Nickel and palladium systems are able to activate all aryl halides, including the less expensive but less reactive chlorides, while copper catalysts can be used for cyanations of aryl iodides and bromides. In this chapter, emphasis is placed on palladium- and copper-based catalysts, taking into account their better ease of execution, their better sustainability, and the high number of systems reported, compared to their nickel counterparts.

Schlüsselwörter

cyanation - aryl halides - arenecarbonitriles - catalysis - homogeneous - cyanide - nickel - palladium - copper - ligand - potassium cyanide - sodium cyanide - zinc cyanide - potassium hexacyanoferrate(II) - cyanohydrin - trimethylsilyl cyanide - poisoning

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