Sequential Pd(0)/Fe(III) Catalyzed Azide-Isocyanide Coupling/Cyclization Reaction: One-Pot Synthesis of Aminotetrazoles

Ramdas S. Pathare, Arshad J. Ansari, Sarika Verma, Anand Maurya, Antim K. Maurya, Vijai K. Agnihotri, Ashoke Sharon, Ram T. Pardasani, Devesh M. Sawant*

*School of Chemical Sciences and Pharmacy, Central University of Rajasthan, NH-8, Bandarsindri, Ajmer-305817, Rajasthan, India, Email: dmscuraj.ac.in

R. S. Pathare, A. J. Ansari, S. Verma, A. Maurya, A. K. Maurya, V. K. Agnihotri, A. Sharon, R. T. Pardasani, D. M. Sawant, J. Org. Chem., 2018, 83, 9530-9537.

DOI: 10.1021/acs.joc.8b01261

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Abstract

Sequential Pd(0)/Fe(III) catalysis enables a rapid and efficient synthesis of aminotetrazoles from aryl azides, isocyanides, and TMSN₃. The reaction sequence utilizes a Pd-catalyzed azide-isocyanide denitrogenative coupling to generate an unsymmetric carbodiimide, which reacts with TMSN₃ in the presence of FeCl₃ in a single pot.

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Key Words

tetrazoles, carbodiimides

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ID: J42-Y2018