Palladium-Catalyzed Asymmetric Suzuki–Miyaura Cross Coupling with Homochiral Phosphine Ligands Having Tetrahydro-1H-imidazo[1,5-a]indole Backbone

Abstract Amphiphilic polystyrene-poly(ethylene glycol) resin-supported chiral imidazoindole phosphines (PS-PEG-L*), (3 R ,9a S )-2-aryl-3-(2-dialkylphosphino)phenyltetrahydro-1 H -imidazo[1,5- a ]indol-1-one, bearing PPh 2 , P( t -Bu) 2 , and P( c -Hex) 2 groups were designed and prepared with a vie...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2016-10, Vol.49 (1), p.59-68
Main Authors: Uozumi, Yasuhiro, Matsuura, Yutaka, Suzuka, Toshimasa, Arakawa, Takayasu, Yamada, Yoichi M. A.
Format: Article
Language:English
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Summary:Abstract Amphiphilic polystyrene-poly(ethylene glycol) resin-supported chiral imidazoindole phosphines (PS-PEG-L*), (3 R ,9a S )-2-aryl-3-(2-dialkylphosphino)phenyltetrahydro-1 H -imidazo[1,5- a ]indol-1-one, bearing PPh 2 , P( t -Bu) 2 , and P( c -Hex) 2 groups were designed and prepared with a view toward using them in aqueous heterogeneous asymmetric Suzuki–Miyaura biaryl coupling. The asymmetric coupling of 2-substituted 1-iodonaphthalenes and 2-substituted naphthalen-1-ylboronic acid took place in water under heterogeneous conditions in the presence of 10 mol% palladium of PS-PEG-L*-Pd complexes to give up to 94% ee of ( S )-2,2′-disubstituted 1,1′-binaphthyls.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1589407