Dual Reactivity of 1,2,3,4-Tetrazole: Manganese-Catalyzed Click Reaction and Denitrogenative Annulation.

Dual Reactivity of 1,2,3,4-Tetrazole: Manganese-Catalyzed Click Reaction and Denitrogenative Annulation. Angew Chem Int Ed Engl. 2020 Sep 14;: Authors: Chattopadhyay B, Khatua H, Das SK, Roy S Abstract A general catalytic method using Mn-porphyrin-based catalytic system is discovered that enables two different reactions (click reaction and denitrogenative annulation) affording two different classes of nitrogen heterocycles, such as 1,5-disubstituted 1,2,3-triazoles (with a pyridyl motif) and 1,2,4-triazolo-pyridines. Mechanistic investigations suggest that while click reaction likely proceeds through an ionic mechanism, which is different from the traditional click reaction, denitrogenative annulation undergoes likely via an electrophilic metallonitrene intermediate rather than the metalloradical intermediate. Collectively, the discovered method is highly efficient that offer obvious advantages over other methods, as it excludes multi-step synthesis of these classes of N-heterocyclic molecules and produces only environmentally benign N2 gas by-product. PMID: 32929858 [PubMed - as supplied by publisher]
Source: Angewandte Chemie - Category: Chemistry Authors: Tags: Angew Chem Int Ed Engl Source Type: research