Unexpected effects of the addition of copper(II) bisphenanthroline complexes in Chan-Lam couplings
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.
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BibTeX
@misc{frappier2026unexpected,
title = {{Unexpected effects of the addition of copper(II) bisphenanthroline complexes in Chan-Lam couplings}},
author = {Émile Frappier and Frank Schaper},
howpublished = {ChemRxiv},
year = {2026},
month = sep,
doi = {10.26434/chemrxiv.15009019/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009019/v1},
note = {CC BY},
}
RIS
TY - UNPB
TI - Unexpected effects of the addition of copper(II) bisphenanthroline complexes in Chan-Lam couplings
AU - Émile Frappier
AU - Frank Schaper
PY - 2026
DA - 2026/09/17
PB - ChemRxiv
DO - 10.26434/chemrxiv.15009019/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009019/v1
AB - 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.
ER -