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Synthesis of Axially Chiral 1,1′‐Binaphthalenes by Palladium‐Catalysed Cross‐Coupling Reactions of Triorganoindium Reagents
Author(s) -
Mosquera Ángeles,
Pena Miguel A.,
Pérez Sestelo José,
Sarandeses Luis A.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300042
Subject(s) - chemistry , reagent , palladium , steric effects , coupling reaction , catalysis , indium , enantiomeric excess , ligand (biochemistry) , enantiomer , combinatorial chemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , biochemistry , receptor
1,1′‐Binaphthalenes and heterocyclic analogues can be efficiently prepared by palladium‐catalysed cross‐coupling reactions between tri(1‐naphthyl)indium reagents and 1‐halonaphthalenes and haloisoquinolines. The reactions were usually carried out in THF at 80 °C with a slight excess of the indium reagent (40 mol‐%) and a low catalyst loading (4 mol‐% Pd) to afford the cross‐coupling products in good yields (45–99 %). The method allows the synthesis of sterically hindered 2‐substituted and 2,2′‐disubstituted 1,1′‐binaphthalenes and naphthylisoquinolines. In addition, the coupling reactions can be performed enantioselectively and the best enantiomeric excesses were obtained by using the chiral amino‐phosphane ferrocenyl ligand ( R , S )‐PPFA.