Herein, an unprecedented photoinduced [3+2] cycloaddition of isobutylene, generated in situ from the Boc group via HFIPpromoted, and carbonyl cyclopropane is reported, enabling access a diverse range of poly-substituted cyclopentane or pyrrolidine derivatives. Mild conditions, simple operation and excellent functional groups tolerance characterize this protocol. Above all, it not only eliminates the hazards linked with the storage and handling of pressurized isobutylene but also highlights the versatility of Boc group as a synthon in complex molecule assembly, providing a strategic advance toward greener and more sustainable synthetic methodologies.

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