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- Title
Regio- and Enantioselective Photodimerization within the Confined Space of a Homochiral Ruthenium/Palladium Heterometallic Coordination Cage.
- Authors
Guo, Jing; Xu, Yao ‐ Wei; Li, Kang; Xiao, Li ‐ Min; Chen, Sha; Wu, Kai; Chen, Xu ‐ Dong; Fan, Yan ‐ Zhong; Liu, Jun ‐ Min; Su, Cheng ‐ Yong
- 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.
- Subjects
ENANTIOSELECTIVE catalysis; RUTHENIUM compounds; PALLADIUM compounds; REGIOSELECTIVITY (Chemistry); PHOTODIMERIZATION; NAPHTHOL derivatives; COORDINATION compounds; PHOTOCHEMISTRY
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 14, p3910
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201611875