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Regio- and Enantioselective Photodimerization within the Confined Space of a Homochiral Ruthenium/Palladium Heterometallic Coordination Cage.

Authors
  • Guo, Jing1
  • Xu, Yao-Wei1
  • Li, Kang1
  • Xiao, Li-Min2
  • Chen, Sha1
  • Wu, Kai
  • Chen, Xu-Dong1
  • Fan, Yan-Zhong1
  • Liu, Jun-Min1
  • Su, Cheng-Yong1
  • 1 MOE Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, and School of Materials Science and Engineering, Sun Yat-Sen University, Guangzhou, 510275, China. , (China)
  • 2 School of Computer Science and Engineering, Beihang University, Beijing, 100191, China. , (China)
Type
Published Article
Journal
Angewandte Chemie International Edition in English
Publisher
Wiley (John Wiley & Sons)
Publication Date
Mar 27, 2017
Volume
56
Issue
14
Pages
3852–3856
Identifiers
DOI: 10.1002/anie.201611875
PMID: 28247533
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The photoinduced regio- and enantioselective coupling of naphthols and derivatives thereof is achieved in the confined chiral coordination space of a RuII metalloligand based cage. The racemic or enantiopure cages encapsulate naphthol guests, which then undergo a regiospecific 1,4-coupling, rather than the normal 1,1-coupling, to form 4-(2-hydroxy-1-naphthyl)-1,2-napthoquinones; moderate stereochemical control is achieved with homochiral cages. The photoreactions proceed under both aerobic and anaerobic conditions but through distinct pathways that nevertheless involve the same radical intermediates. This unusual dimerization constitutes a very rare example of asymmetric induction in biaryl coupling by making use of coordination cages with dual functionality-photoredox reactivity and stereoselectivity. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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