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DOI: 10.1055/s-0036-1589407
Palladium-Catalyzed Asymmetric Suzuki–Miyaura Cross Coupling with Homochiral Phosphine Ligands Having Tetrahydro-1H-imidazo[1,5-a]indole Backbone
Publikationsverlauf
Received: 30. September 2016
Accepted after revision: 07. Oktober 2016
Publikationsdatum:
27. Oktober 2016 (online)
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The authors would like to dedicate this article to Professor Dieter Enders on the occasion of his 70th birthday.
Abstract
Amphiphilic polystyrene-poly(ethylene glycol) resin-supported chiral imidazoindole phosphines (PS-PEG-L*), (3R,9aS)-2-aryl-3-(2-dialkylphosphino)phenyltetrahydro-1H-imidazo[1,5-a]indol-1-one, bearing PPh2, 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.
Key words
asymmetric catalysis - biaryls - cross-coupling - palladium - Suzuki–Miyaura coupling - catalysis in water - heterogeneous catalysisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589407.
Included are NMR charts, HPLC data, and the CIF file of L*1-PdCl2
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- Supporting Information
- CIF File
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For reviews, see:
Alkylation:
Amination:
Cyclization:
Etherification:
Nitromethylation:
Enantioselective desymmetrization:
For nonasymmetric Suzuki–Miyaura coupling in water with PS-PEG resin-supported Pd complexes, see:
For recent reviews, see:
For pioneering studies on the asymmetric Suzuki–Miyaura coupling, see:
For a review on asymmetric cross-coupling, see:
For examples for highly stereoselective Suzuki–Miyaura coupling, see: