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The combination of electron-rich diaminoalkynes and ditopic Lewis acids diboranes(4) leads to unusual uncatalysed diboration reactions involving internal Lewis adduct, zwitterion, and C–C bond formation. The products are novel multicyclic, charge-separated compounds with intramolecular dative bonds.

Graphical abstract: Alkylideneborate zwitterions and C–C coupling by atypical diboration of electron-rich alkynes

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