Demonstrates a stable Lewis adduct's reactivity with various organic compounds, suggesting new transformation pathways.
A stable intramolecular Lewis adduct 1 was prepared by hydroboration of 2-diphenylphosphinobenzaldehyde with HB(C₆F₅)₂. Despite its intramolecular Lewis pairing, 1 exhibits pronounced frustrated Lewis pair-type reactivity toward aldehydes, alkynes, azides, and isocyanides, enabling diverse transformations. Isolated products include aldehyde 1,2-addition derivatives (2-4), head-to-tail dimerized alkyne adducts (5 and 6), Staudinger-type phosphinimine (7), Lewis adducts of isocyanides (8 and 9), and the [4 + 2] cycloaddition product (10) from 2-isocyanonaphthalene. All compounds were fully characterized, and the reaction mechanism is also considered.
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Li et al. (2026) studied this question.
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