Benzene rings are some of the most prevalent ring systems found in small molecule drugs with only a few dominant substitution patterns (1-, 1,2-, 1,4-, and 1,2,4-). Traditional and contemporary synthetic strategies to prepare underrepresented, highly substituted arenes have limited generality.  Development of a convergent benzannulation through [2+2+2] alkyne cyclotrimerization is a straightforward atom economical approach to access highly substituted arenes; however, issues of regioselectivity and competing benzannulation pathways have plagued past methods. Vinyl sulfone, a recognized alkyne surrogate, has electronic and steric properties that offer unique opportunities in transition-metal-catalyzed benzannulation chemistry. Stoichiometric and catalytic studies of two- and three-component nickel-catalyzed cyclotrimerization with alkynes and vinyl sulfone to synthesize multi-substituted arenes will be discussed.

Nickel-catalyzed cyclotrimerization of alkynes with vinyl sulfone partners

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