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Dual Reactivity of 1,2,3,4‐Tetrazole: Manganese‐Catalyzed Click Reaction and Denitrogenative Annulation
Author(s) -
Khatua Hillol,
Das Sandip Kumar,
Roy Satyajit,
Chattopadhyay Buddhadeb
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009078
Subject(s) - annulation , chemistry , click chemistry , catalysis , combinatorial chemistry , tetrazole , reactivity (psychology) , electrophile , manganese , ionic bonding , cycloaddition , molecule , photochemistry , organic chemistry , ion , medicine , alternative medicine , pathology
A general catalytic method using a Mn‐porphyrin‐based catalytic system is reported that enables two different reactions (click reaction and denitrogenative annulation) and affords two different classes of nitrogen heterocycles, 1,5‐disubstituted 1,2,3‐triazoles (with a pyridyl motif) and 1,2,4‐triazolo‐pyridines. Mechanistic investigations suggest that although the click reaction likely proceeds through an ionic mechanism, which is different from the traditional click reaction, the denitrogenative annulation reaction likely proceeds via an electrophilic metallonitrene intermediate rather than a metalloradical intermediate. Collectively, this method is highly efficient and offers several advantages over other methods. For example, this method excludes a multi‐step synthesis of the N‐heterocyclic molecules described and produces only environmentally benign N 2 gas a by‐product.