The challenge of palladium-catalyzed aromatic azidocarbonylation: from mechanistic and catalyst deactivation studies to a highly efficient process

…, J Benet-Buchholz, VI Bakhmutov, SA Macgregor…

Index: Miloserdov, Fedor M.; McMullin, Claire L.; Belmonte, Marta Martinez; Benet-Buchholz, Jordi; Bakhmutov, Vladimir I.; Macgregor, Stuart A.; Grushin, Vladimir V. Organometallics, 2014 , vol. 33, # 3 p. 736 - 752

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Citation Number: 12

Abstract

Azidocarbonylation of iodoarenes with CO and NaN3, a novel Heck-type carbonylation reaction, readily occurs in an organic solvent–H2O biphasic system to furnish aroyl azides at room temperature and 1 atm. The reaction is catalyzed by Xantphos-Pd and exhibits high functional group tolerance. The catalyst deactivation product,[(Xantphos) PdI2], can be reduced in situ with PMHS to Pd (0) to regain catalytic activity. In this way, the catalyst ...