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Rhodium-Catalyzed Addition of Organozinc Iodides to Carbon-11 Isocyanates

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journal contribution
posted on 24.03.2020, 15:03 by Braeden A. Mair, Moustafa H. Fouad, Uzair S. Ismailani, Maxime Munch, Benjamin H. Rotstein
Amides were prepared using rhodium-catalyzed coupling of organozinc iodides and carbon-11 (11C, t1/2 = 20.4 min) isocyanates. Nonradioactive isocyanates and sp3 or sp2 organozinc iodides generated amides in yields of 13%–87%. Incorporation of cyclotron-produced [11C]­CO2 into 11C-amide products proceeded in yields of 5%–99%. The synthetic utility of the methodology was demonstrated through the isolation of [11C]N-(4-fluorophenyl)-4-methoxybenzamide ([11C]6g) with a molar activity of 267 GBq μmol–1 and 12% radiochemical yield in 21 min from the beginning of synthesis.