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Regio‐ and Enantioselective Photodimerization within the Confined Space of a Homochiral Ruthenium/Palladium Heterometallic Coordination Cage
Author(s) -
Guo Jing,
Xu YaoWei,
Li Kang,
Xiao LiMin,
Chen Sha,
Wu Kai,
Chen XuDong,
Fan YanZhong,
Liu JunMin,
Su ChengYong
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201611875
Subject(s) - enantiopure drug , enantioselective synthesis , chemistry , palladium , ruthenium , stereochemistry , stereoselectivity , reactivity (psychology) , asymmetric induction , regioselectivity , combinatorial chemistry , cage , stereoisomerism , axial chirality , organic chemistry , molecule , catalysis , medicine , alternative medicine , mathematics , pathology , combinatorics
Abstract The photoinduced regio‐ and enantioselective coupling of naphthols and derivatives thereof is achieved in the confined chiral coordination space of a Ru II 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.