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Regio‐ and Enantioselective Photodimerization within the Confined Space of a Homochiral Ruthenium/Palladium Heterometallic Coordination Cage
Ist Teil von
Angewandte Chemie International Edition, 2017-03, Vol.56 (14), p.3852-3856
Auflage
International ed. in English
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2017
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
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.
Confined coordination spaces in redox‐active ruthenium(II) cages enable the photoinduced regio‐ and enantioselective coupling of naphthol and derivatives thereof. The photoreactions proceed under both aerobic and anaerobic conditions but by distinct pathways that nevertheless involve the same radical intermediates.