Photo-cycloaddition reactions of vinyldiazo compounds

Ming Bao, Klaudia Łuczak, Wojciech Chaładaj (), Marriah Baird, Dorota Gryko () and Michael P. Doyle ()
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Ming Bao: The University of Texas at San Antonio
Klaudia Łuczak: Institute of Organic Chemistry Polish Academy of Sciences
Wojciech Chaładaj: Institute of Organic Chemistry Polish Academy of Sciences
Marriah Baird: The University of Texas at San Antonio
Dorota Gryko: Institute of Organic Chemistry Polish Academy of Sciences
Michael P. Doyle: The University of Texas at San Antonio

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Heterocyclic rings are important structural scaffolds encountered in both natural and synthetic compounds, and their biological activity often depends on these motifs. They are predominantly accessible via cycloaddition reactions, realized by either thermal, photochemical, or catalytic means. Various starting materials are utilized for this purpose, and, among them, diazo compounds are often encountered, especially vinyldiazo compounds that give access to donor-acceptor cyclopropenes which engage in [2+n] cycloaddition reactions. Herein, we describe the development of photochemical processes that produce diverse heterocyclic scaffolds from multisubstituted oximidovinyldiazo compounds. High chemoselectivity, good functional group tolerance, and excellent scalability characterize this methodology, thus predisposing it for broader applications. Experimental and computational studies reveal that under light irradiation these diazo reagents selectively transform into cyclopropenes which engage in cycloaddition reactions with various dipoles, while under thermal conditions the formation of pyrazole from vinyldiazo compounds is favored.

Date: 2024
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DOI: 10.1038/s41467-024-48274-5

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