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Facile syntheses of building blocks for the construction of phosphotyrosine mimetics

Cockerill, G Stuart and Easterfield, Howard J and Percy, Jonathan and Pintat, Stephanie (2000) Facile syntheses of building blocks for the construction of phosphotyrosine mimetics. Journal of the Chemical Society, Perkin Transactions 1, 2000 (16). pp. 2591-2599. ISSN 1472-7781

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The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used to enter the classical organometallic coupling repertoire via Stille and Suzuki–Miyaura couplings. 1,4-Diiodobenzene underwent coupling with the organozinc reagent derived from diethyl bromodifluoromethylphosphonate with copper(I) catalysis to afford diethyl (4-iodophenyl)difluoromethylphosphonate. Higher yielding couplings were run with (4-trifluoromethylsulfonyloxy)- and (4-nonafluorobutylsulfonyloxy)-iodobenzenes. The iodide and the triflate coupled under palladium-catalysed conditions with a range of stannanes and boronic acids in moderate to excellent yields. Shibuya–Yokomatsu couplings were also successful with more functionalised iodoarenes and heteroarenes presenting the important phosphate mimic on a range of scaffolds.