This synthesis demonstrates regioselective nickel-catalyzed cyclotrimerization of alkynes and vinyl sulfones, suggesting a new approach for creating meta-terphenyl derivatives.
Phenyl vinyl sulfone serves as an acetylene surrogate for the regiocontrolled synthesis of meta-terphenyl derivatives. Benzene rings are among the most frequently encountered ring systems in small molecule drugs, but only a few substitution patterns (1-, 1,2-, 1,4-, and 1,2,4-) predominate. Here, regioselective nickel-catalyzed three-component cyclotrimerization (3CC) of terminal alkynes and phenyl vinyl sulfone was used to synthesize an underrepresented substitution pattern, the 1,3-arene. The 3CC reaction demonstrates wide functional group tolerance with moderate to good yields. Stoichiometric reactivity studies with catalytically relevant nickel complexes establish the mechanistic origin of the observed regioselectivity.
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Long et al. (2025) studied this question.
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