Synthesis and Mechanistic Investigation of Bipyrazolo[1,5‑<i>a</i>]pyridines <i>via</i> Palladium-Catalyzed Cross-Dehydrogenative Coupling of Pyrazolo[1,5‑<i>a</i>]pyridines
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The synthesis of a range of 3,3′-bipyrazolo[1,5-a]pyridine derivatives via direct cross-dehydrogenative coupling of pyrazolo[1,5-a]pyridine precursors is herein presented. This simple and efficient methodology involving palladium(II)-catalyzed C–H bond activation showed good functional group tolerance and product yield (up to 94%). Through the mechanistic insights gained from both kinetic isotope effect experimental studies and density functional theory calculations, a plausible reaction mechanism was outlined. Furthermore, subsequent derivatizations of the resulting 7,7′-diaryl-3,3′-bipyrazolo[1,5-a]pyridines, executed by performing palladium-mediated ortho C–H bond activation followed by hypervalent iodine-induced chlorination, rendered this series of compounds more extended π-conjugation and twisted conformations. Our study on these bipyrazolo[1,5-a]pyridine-based luminogens provides new opportunities for tailor-made organic luminescent materials.
