Seßler M, Schatz J (2012)
Publication Type: Journal article, Original article
Publication year: 2012
Original Authors: Seßler M., Schatz J.
Publisher: Wiley-VCH Verlag: No OnlineOpen
Book Volume: 46
Pages Range: 48-59
Journal Issue: 1
Water has attracted significant attention as an alternative solvent for organometallic reactions because it is nontoxic, nonflammable, and inexpensive, and is easily separated from organic products. Organometallic reactions, like the palladium-catalyzed couplings of organic halides with organoboron compounds (Suzuki) and organotin reagents (Stille), are among the most widely used reactions for the formation of carbon-carbon bonds. Owing to the discovery of water-soluble, sulfonated phosphane derivatives and particularly the design of water-soluble palladium-catalysts it was possible to import these reactions into aqueous media. Another efficient, metal-catalyzed, carbon-carbon bond-forming process that is nowadays possible in aqueous media is the olefin metathesis. The approaches so far include the use of water-soluble ruthenium-catalysts, surfactants and additives, ultrasonication, the introduction of polar quaternary ammonium groups or the incorporation of PEG as a water solubilizing moiety. The last point bears also a great potential for further developments in the removal of ruthenium-containing byproducts. Additionally, water is the ideal reaction environment for polar, water soluble substrates such as natural product or pharmaceuticals. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
APA:
Seßler, M., & Schatz, J. (2012). C-C couplings: Organometallic reactions in water. Chemie in Unserer Zeit, 46(1), 48-59. https://dx.doi.org/10.1002/ciuz.201200559
MLA:
Seßler, Miriam, and Jürgen Schatz. "C-C couplings: Organometallic reactions in water." Chemie in Unserer Zeit 46.1 (2012): 48-59.
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