Synthesis and characterisation of homoleptic 2,9-diaryl-1,10-phenanthroline copper(i) complexes: influencing selectivity in photoredox-catalysed atom-transfer radical addition reactions

Dalton Transactions : an International Journal of Inorganic Chemistry
Thomas P NichollsAlex C Bissember

Abstract

This report details the synthesis and characterisation of eight homoleptic bis(2,9-diaryl-1,10-phenanthroline)copper(i) complexes, seven of which are previously unreported {aryl = p-CF3C6H4, p-FC6H4, m,p-(OMe)2C6H3, o,p-(OMe)2C6H3, p-OMe-m,m-Me2C6H2, p-OMe-m,m-(t-Bu)2C6H2, 9,9-dimethyl-9H-fluoren-2-yl, 4-(9H-carbazol-9-yl)phenyl)}. Where possible the solid state, photophysical and electrochemical properties of these complexes were studied. In order to obtain insights into the influence of the intrinsic features of these copper(i) complexes on their reactivity in visible light-mediated photoredox catalysis, their capacity to promote a known atom-transfer radical addition process was evaluated. This specific transformation was identified as a suitable model system as it is reported to proceed via a mechanism consistent with the inner-sphere reactivity enabled by coordinatively unsaturated phenanthroline-based copper(i) species.

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Citations

Aug 8, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Thomas P NichollsAlex C Bissember
Apr 11, 2020·Beilstein Journal of Organic Chemistry·Mingbing ZhongThomas Poisson
Nov 27, 2019·Inorganic Chemistry·Gautam D StroscioRyan G Hadt
Aug 30, 2019·Journal of the American Chemical Society·Patrick HerrOliver S Wenger

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Methods Mentioned

BETA
X-ray
column chromatography
NMR

Software Mentioned

SHELXL
SHELXT
97
Nova
SQUEEZE

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