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Abstract

Photoredox-mediated Ni-catalyzed cross-couplings are powerful transformations to form carbon–heteroatom bonds and are generally photocatalyzed by noble metal complexes. Low-cost and easy-to-prepare carbon dots (CDs) are attractive quasi-homogeneous photocatalyst alternatives, but their applicability is limited by their short photoluminescence (PL) lifetimes. By tuning the surface and PL properties of CDs, we designed colloidal CD nano-photocatalysts for a broad range of Ni-mediated cross-couplings between aryl halides and nucleophiles. In particular, a CD decorated with amino groups permitted coupling to a wide range of aryl halides and thiols under mild, base-free conditions. Mechanistic studies suggested dynamic quenching of the CD excited state by the Ni co-catalyst and identified that pyridinium iodide (pyHI), a previously used additive in metallaphotocatalyzed cross-couplings, can also act as a photocatalyst in such transformations.