Halocyclization reaction represents one of the most common methodologies for the synthesis of heterocyclic molecules. Many efforts have been developed to balance the relationship between structure, reactivity and selectivity, including the design of new electrophilic halogenation reagents and the utilization of activating strategies. However, the universality of reagents or activating strategies for electrophilic halocyclization remains challenging due to the case-by-case practice for different substrates or different cyclization models. Here we report an intramolecular chaperone-assisted dual-anchoring activation (ICDA) model for electrophilic halocyclization, taking advantage of non-covalent dual-anchoring orientation as the driving force. This protocol allows a practical, catalyst-free and rapid approach to access seven types of small-sized, medium-sized, large-sized heterocyclic units and to realize polyene-like domino halocyclizations, as exemplified on nearly 90 examples, including a risk-reducing flow protocol for gram-scale synthesis. DFT studies verify the crucial role of ICDA in affording a suitable preorganization for the transition state stabilization and "X" ^"+" transfer acceleration. The utilization of ICDA model allows a spatiotemporal adjustment to straightforward obtain fast, selective and high-yielding synthetic transformations.

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