Bu₄NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters

Suresh Rajamanickam, Chitranjan Sah, Bilal Ahmad Mir, Subhendu Ghosh, Garima Sethi, Vinita Yadav, Sugumar Venkataramani* and Bhisma K. Patel*

*IISER Mohali, Knowledge City, Sector 81, Manauli, SAS Nagar 140306; Indian Institute of Technology Guwahati, Guwahati 781039, India, Email: sugumarviisermohali.ac.in, pateliitg.ac.in

S. Rajamanickam, C. Sah, B. A. Mir, S. Ghosh, G. Sethi, V. Yadav, S. Venkateramani, B. K. Patel, J. Org. Chem., 2020, 85, 2118-2141.

DOI: 10.1021/acs.joc.9b02875

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Abstract

Bu₄NI catalyzes regioselective N²-alkylations and N²-arylations of tetrazoles using tert-butyl hydroperoxide as a methyl source, alkyl diacyl peroxides as primary alkyl source, alkyl peresters as secondary and tertiary alkyl sources, and aryl diacyl peroxides as arylating source. These reactions proceed without pre-functionalization of the tetrazoles and in the absence of any metal catalysts.

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Key Words

N-alkylations, N-arylations, tetrazoles

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ID: J42-Y2020