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Unexpected effects of the addition of copper(II) bisphenanthroline complexes in Chan-Lam couplings

Year: 2026

Type: preprint

Abstract: The effect of the addition of bis(2,9-dimethyl-1,10-phenanthroline)copper(II) chloride and bis(1,10-phenanthroline)copper(II) chloride on Chan-Lam couplings with copper acetate and a previously reported coordination complex LCuCl were investigated with respect to their potential role as redox shuttles in the catalytic cycle. In neither case action as a redox shuttle was observed. While no effects were observed in reactions catalysed by LCuCl, addition to reactions catalyzed by copper acetate gave more complicated results, sometimes with drastically increased activity. Detailed investigations found that (i) ligand exchange results in the formation of a more active mono-phenanthroline copper complex and (ii) formation of mixed chloride/acetate salts lead to significant increases in activity. This result could not be generalized for a wider range of N-nucleophiles or observed for anion combinations other than chloride/acetate.

Source: ChemRxiv

DOI: 10.26434/chemrxiv.15009019/v1

Authors: Émile Frappier, Frank Schaper

Institutions: Centre in Green Chemistry and Catalysis, Université de Montréal

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Centre in Green Chemistry and Catalysis, Natural Sciences and Engineering Research Council of Canada

Awards: G2614460161, G3970872308, Electrochemically-driven Chan-Lam coupling reactions

OpenAlex ID: W7213535070

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