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

Yasuhiro Uozumi; Yutaka Matsuura; Toshimasa Suzuka; Takayasu Arakawa; Yoichi M. A. Yamada

doi:10.1055/s-0036-1589407

Synthesis, Table of Contents

Synthesis 2017; 49(01): 59-68
DOI: 10.1055/s-0036-1589407

paper

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

Yasuhiro Uozumi*

^aHubei Key Laboratory of Natural Products Research and Development, China Three Gorges University, Yichang 443002, P. R. of China

^bInstitute for Molecular Science (IMS), Myodaiji, Okazaki 444-8787, Japan

^cSOKENDAI (The Graduate University for Advanced Studies), Okazaki 444-8787, Japan

^dRiken Center for Sustainable Resource Science, 2-1 Hirowasa, Wako 351-0198, Japan Email: uo@ims.ac.jp

,

Yutaka Matsuura

^bInstitute for Molecular Science (IMS), Myodaiji, Okazaki 444-8787, Japan

,

Toshimasa Suzuka

^bInstitute for Molecular Science (IMS), Myodaiji, Okazaki 444-8787, Japan

,

Takayasu Arakawa

^bInstitute for Molecular Science (IMS), Myodaiji, Okazaki 444-8787, Japan

^cSOKENDAI (The Graduate University for Advanced Studies), Okazaki 444-8787, Japan

,

Yoichi M. A. Yamada

^dRiken Center for Sustainable Resource Science, 2-1 Hirowasa, Wako 351-0198, Japan Email: uo@ims.ac.jp

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Abstract

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The authors would like to dedicate this article to Professor Dieter Enders on the occasion of his 70^th 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 catalysis

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References

References

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