Highly selective oxidative cross-coupling polymerization with copper(I)-bisoxazoline catalysts

The asymmetric oxidative coupling polymerization of methyl 6,6'-dihydroxy-2,2'-binaphthalene-7-carboxylate with the copper-diamine catalysts under an O 2 atmosphere was carried out. As is the case with the CuCl-2,2'-(S)-isopropylidenbis(4-phenyl-2-oxazoline) [(S)IPhO] catalyst, a polymer with a high cross-coupling selectivity of 96% was obtained in 71% yield, whose THF-soluble part had a number-average molecular weight of 4.5 x 10 3 . To estimate the enantioselectivity with respect to the cross-coupling linkage in the obtained polymer, the model asymmetric oxidative cross-coupling reaction with CuCl-(S)IPhO was also conducted, and the products showed a 94% cross-coupling selectivity and enantioselectivity of 31% ee (S).

[1]  D. Ha,et al.  Enantioselective oxidative coupling of methyl 3-hydroxy-2-naphthoate using mono-N-alkylated octahydrobinaphthyl-2,2′-diamine ligand , 2004 .

[2]  Hiroharu Ajiro,et al.  Asymmetric oxidative coupling polymerization affording polynaphthylene with 1,1′‐bi‐2‐naphthol units , 2004 .

[3]  K. Fuji,et al.  Configurationally defined sexi- and octinaphthalene derivatives: synthesis and optical properties , 2004 .

[4]  A. Martell,et al.  Structurally defined catalysts for enantioselective oxidative coupling reactions. , 2003, Angewandte Chemie.

[5]  Y. Okamoto,et al.  Synthesis of poly(1,4-naphthylene) bearing crown ether side chain by asymmetric oxidative coupling polymerization , 2003 .

[6]  Hiroharu Ajiro,et al.  Stereoselective Synthesis of (R,R)-, (S,S)-, and (R,S)-Poly(2,3- dihydroxy-1,4-naphthylene) Derivatives by Asymmetric Oxidative Coupling Polymerization , 2003 .

[7]  Carol A. Mulrooney,et al.  Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: efficient formation of chiral functionalized BINOL derivatives. , 2003, The Journal of organic chemistry.

[8]  M. Kozlowski,et al.  Novel pathways for the formation of chiral binaphthyl polymers: oxidative asymmetric phenolic coupling alone and in tandem with the Glaser-Hay coupling. , 2003, Angewandte Chemie.

[9]  Y. Okamoto,et al.  Copper(I)-Catalyzed Asymmetric Oxidative Coupling Polymerization of 2,3-Dihydroxynaphthalene Using Bisoxazoline Ligands , 2003 .

[10]  Chang-Ying Chu,et al.  Catalytic enantioselective coupling of 2-naphthols by new chiral oxovanadium complexes bearing a self accelerating functional group , 2003 .

[11]  Chien-Tien Chen,et al.  Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates. , 2002, Organic letters.

[12]  X. Cui,et al.  The rational design of novel chiral oxovanadium(IV) complexes for highly enantioselective oxidative coupling of 2-naphthols. , 2002, Chemical communications.

[13]  Wenbin Lin,et al.  Well-defined enantiopure 1,1'-binaphthyl-based oligomers: synthesis, structure, photophysical properties, and chiral sensing. , 2002, The Journal of organic chemistry.

[14]  Y. Okamoto,et al.  Asymmetric Oxidative Coupling Polymerization of Optically Active Tetrahydroxybinaphthalene Derivative , 2002 .

[15]  Xiao-Li Yan,et al.  Synthesis and Study of Optically Active Polydendrimers , 2001 .

[16]  J. Yang,et al.  Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes. , 2001, Organic letters.

[17]  Y. H. Liu,et al.  Catalytic asymmetric coupling of 2-naphthols by chiral tridentate oxovanadium (IV) complexes. , 2001, Organic letters.

[18]  Chang-Ying Chu,et al.  Chiral oxovanadium complex catalyzed enantioselective oxidative coupling of 2-naphthols , 2001 .

[19]  L. Pu.  Novel chiral conjugated macromolecules for potential electrical and optical applications , 2000 .

[20]  K. Koga,et al.  Enantioselective synthesis of binaphthol derivatives by oxidative coupling of naphthol derivatives catalyzed by chiral diamine-copper complexes , 1999 .

[21]  Lin Pu,et al.  1,1'-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials. , 1998, Chemical reviews.

[22]  S. Vyskocil,et al.  On the ‘Novel two-phase oxidative cross-coupling of the two-component molecular crystal of 2-naphthol and 2-naphthylamine’ , 1998 .

[23]  K. Ding,et al.  NOVEL TWO-PHASE OXIDATIVE CROSS-COUPLING OF THE TWO-COMPONENT MOLECULAR CRYSTAL OF 2-NAPHTHOL AND 2-NAPHTHYLAMINE , 1997 .

[24]  K. Tanaka,et al.  Preparation and absolute configuration of hexahydroxyter- and octahydroxyquaternaphthalene derivatives , 1996 .

[25]  Shunichi Hashimoto,et al.  Catalytic asymmetric synthesis of binaphthol derivatives by aerobic oxidative coupling of 3-hydroxy-2-naphthoates with chiral diamine-copper complex , 1995 .

[26]  T. A. Claxton,et al.  Selective Cross-Coupling of 2-Naphthol and 2-Naphthylamine Derivatives. A Facile Synthesis of 2,2',3-Trisubstituted and 2,2',3,3'-Tetrasubstituted 1,1'-Binaphthyls , 1994 .

[27]  S. Vyskocil,et al.  Synthesis of enantiomerically pure binaphthyl derivatives. Mechanism of the enantioselective, oxidative coupling of naphthols and designing a catalytic cycle , 1993 .

[28]  H. Kung,et al.  Synthesis and characterization of iodobenzamide analogues: potential D-2 dopamine receptor imaging agents. , 1990, Journal of medicinal chemistry.

[29]  Jana Günterová,et al.  Highly selective oxidative cross-coupling of substituted 2-naphthols: A convenient approach to unsymmetrical 1,1′-binaphthalene-2,2′-diols , 1990 .

[30]  Koji Yamamoto,et al.  Synthesis and chiral recognition of an optically active bis-crown ether incorporating a diphenanthrylnaphthalene moiety as the chiral centre , 1987 .