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Reactions of thermally generated benzynes with six-membered N-heteroaromatics: pathway and product diversity

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Abstract

We report here various pathways by which six-membered N-heteroaromatic compounds react with benzynes that are generated by the HDDA reaction. The initially formed 1,3-zwitterionic species (a) can collapse intramolecularly to give novel 1 : 1 adducts of the heterocycle and benzyne; (b) can react with an externally added, electrophilic third-component to give functionalized heterocyclic products; or (c) can react with an external protic nucleophile to produce, following collapse of the ion pair resulting from protonation of the zwitterion, a variety of three-component assemblies. Mechanisms for formation of some of the 1 : 1 adducts are supported by DFT methods. The scope of the protic nucleophilic coupling was also expanded to a two-pot operation by using triflic acid as a protic “non-nucleophile”, followed by the addition of a suitably reactive nucleophile.

Graphical abstract: Reactions of thermally generated benzynes with six-membered N-heteroaromatics: pathway and product diversity

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Publication details

The article was received on 13 Jul 2019, accepted on 13 Aug 2019 and first published on 14 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03479J
Chem. Sci., 2019, Advance Article
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    Reactions of thermally generated benzynes with six-membered N-heteroaromatics: pathway and product diversity

    S. Arora, J. Zhang, V. Pogula and T. R. Hoye, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03479J

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