Highly substituted benzene rings are extensively found in pharmaceutically relevant compounds. Alkyne [2+2+2] cycloaddition is an optimal method for producing highly substituted benzene rings; however, regiocontrol remains persistent issue. Symmetrical alkyne substrates or intramolecular reaction variants, frequently involving a diyne reaction partner, are often used to minimize issues of regiocontrol. Alkyne surrogates, such as vinyl sulfone, have unique steric and electronic characteristics that open new opportunities in cyclotrimerization chemistry. Results of nickel-catalyzed three component [2+2+2] cyclotrimerization, featuring vinyl sulfone and aryl alkynes, that produce exclusively 1,3-diarylbenzene products in good-to-excellent yield will be presented.

Nickel-catalyzed cyclotrimerization of terminal alkynes with vinyl sulfone

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ACS Fall 2022

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