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

Nicholls, TP ORCID: 0000-0001-6654-0825, Caporale, C, Massi, M, Gardiner, MG ORCID: 0000-0001-6373-4253 and Bissember, AC ORCID: 0000-0001-5515-2878 2019 , '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, vol. 48 , pp. 7920-7301 , doi: 10.1039/c8dt04116d.

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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.

Item Type: Article
Authors/Creators:Nicholls, TP and Caporale, C and Massi, M and Gardiner, MG and Bissember, AC
Keywords: photoredox catalysis, copper, atom-transfer radical addition
Journal or Publication Title: Dalton Transactions
Publisher: Royal Soc Chemistry
ISSN: 1477-9226
DOI / ID Number: 10.1039/c8dt04116d
Copyright Information:

Copyright 2019 The Royal Society of Chemistry

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