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Chemical study demonstrates copper-promoted difluoroalkylative alkynylation of [3.1.1]propellane, enabling modular synthesis of functionalized bicyclo[3.1.1]heptanes for drug discovery.
Bicyclo[3.1.1]heptane (BCHep) is a rigid three-dimensional bioisostere of meta-substituted benzene, yet functionalized derivatives remain scarce. We report a copper-promoted three-component difluoroalkylative alkynylation of [3.1.1]propellane with terminal alkynes and bromodifluoroacetates, enabling simultaneous installation of a gem-difluoro group and a versatile alkyne handle at the bridgehead. This one-step transformation provides modular access to difunctionalized BCHep scaffolds under mild conditions with broad functional group tolerance and offers opportunities for late-stage diversification of complex molecules.
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Huang et al. (2026) studied this question.
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