Abstract
Amphiphilic polystyrene-poly(ethylene glycol) resin-supported chiral imidazoindole phosphines (PS-PEG-L*), (3<i>R</i>,9a<i>S</i>)-2-aryl-3-(2-dialkylphosphino)phenyltetrahydro-1<i>H</i>-imidazo[1,5-<i>a</i>]indol-1-one, bearing PPh<sub>2</sub>, P(<i>t</i>-Bu)<sub>2</sub>, and P(<i>c</i>-Hex)<sub>2</sub> 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 (<i>S</i>)-2,2′-disubstituted 1,1′-binaphthyls.
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