Synthesis of novel nitrogen-containing polymers by Pd(0)-catalyzed polycondensation of propargylic carbonates and bifunctional nitrogen nucleophiles

European Polymer Journal

Volumn 47, Issue 5, 2011, Pages 1142-1150

  Nishioka, Noriyuki ^a   Koizumi, Toshio ^a  

^a NATIONAL DEFENSE ACADEMY   (Japan)

Author keywords

Nitrogen nucleophile; Nitrogen containing polymer; Palladium catalysis; Polycondensation; Polymerization behavior

Indexed keywords

AROMATIC AMINES; ARYL GROUP; BIFUNCTIONAL; DIIMIDE; NITROGEN NUCLEOPHILES; PALLADIUM CATALYSIS; PHENYL ETHERS; POLYMERIZATION BEHAVIOR;

AMINES; AROMATIC POLYMERS; CARBONATES; CATALYSIS; ETHERS; NITROGEN; NUCLEOPHILES; POLYCONDENSATION;

POLYMERS;

EID: 79954605821     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2011.01.014     Document Type: Article

References (29)

1. J. Tsuji Palladium reagents and catalysts, New perspectives for the 21st century 2004 Chichester UK, Wiley p. 431-511
2. M. Suzuki, S. Sawada, S. Yoshida, A. Eberhardt, and T. Saegusa New ring-opening polymerization via a π-allylpalladium complex. 2. Novel proton-transfer polymerization of vinylcyclopropane derivatives having two electron-withdrawing substituents Macromolecules 26 1993 4748 4750
3. N. Miyaki, I. Tomita, and T. Endo Coupling polymerization of monofunctional allene derivatives with malonates bearing aryl halides moieties via π-allylpalladium complex J Polym Sci A: Polym Chem 35 1997 2097 2103 (Pubitemid 127576728)
4. N. Nomura, N. Yoshida, K. Tsurugi, and K. Aoi Versatile carbon-carbon bond-forming polycondensation and malonic esters via palladium-catalyzed allylic substitution reaction Macromolecules 36 2003 3007 3009
5. T. Koizumi, J. Sakamoto, Y. Gondo, and T. Endo Novel palladium(0)- catalyzed polyaddition of bifunctional vinyloxiranes with 1,3-diketones. Synthesis of new polymers bearing an allyl alcohol moiety via π-allylpalladium intermediates Macromolecules 35 2002 2898 2902 (Pubitemid 34586511)
6. T. Koizumi, J. Sakamoto, Y. Gondo, and T. Endo Pd(0)-catalyzed polyaddition of bifunctional vinyloxiranes with 1,3-dicarbonyl compounds: the synthesis of polymers containing hydroxy and carbonyl groups J Polym Sci A: Polym Chem 40 2002 2487 2494
7. T. Koizumi, T. Imai, and T. Endo Pd(0)-catalyzed polyaddition of bifunctional vinyloxiranes with phenol derivatives: The synthesis of polymers containing an allyl aryl ether moiety in the main chain J Polym Sci A: Polym Chem 41 2003 476 482 (Pubitemid 36239134)
8. T. Koizumi, Y. Koma, and T. Endo Palladium(0)-catalyzed polyaddition of bifunctional vinyloxirane with nitrogen nucleophiles synthesis of polymers containing an allylamine moiety in the main chain and pendant hydroxyl groups Macromolecules 36 2003 5882 5884
9. N. Nomura, S. Komiyama, H. Kasugai, and M. Saba An efficient protocol of iridium-catalyzed allylic substitution reaction and its application to polymer synthesis: complementary regio- and stereoselective allylation polycondensation via Ir and Pd catalyses J Am Chem Soc 130 2008 812 814
10. J. Tsuji, and T. Mandai Palladium-catalyzed reactions of propargylic compounds in organic synthesis Angew Chem Int Ed Engl 34 1995 2589 2612 (Pubitemid 126675728)
11. J. Tsuji, H. Watanabe, I. Minami, and I. Shimizu Novel palladium-catalyzed reactions of propargylic carbonates with carbon nucleophiles under neutral conditions J Am Chem Soc 107 1985 2196 2198
12. I. Minami, M. Yuhara, H. Watanabe, and J. Tsuji A new furan annelation reaction by the palladium-catalyzed reaction of 2-alkynyl carbonates or 2-(1lkynyl)oxiranes with β-keto esters J Organomet Chem 334 1987 225 242
13. J.-R. Labrosse, P. Lhoste, and D. Sinou Palladium-catalyzed synthesis of 2,3-dihydro-2-ylidene-1,4-benzodioxins J Org Chem 66 2001 6634 6642 (Pubitemid 32946580)
14. I. Ambrogio, S. Cacchi, G. Fabrizi, and A. Prastaro 3-(o- Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles Tetrahedron 65 2009 8916 8929
15. X.-H. Duan, L.-N. Guo, H.-P. Bi, X.-Y. Liu, and Y.-M. Liang Highly regioselective synthesis of 2, 3-disubstituted indenes via a novel palladium-catalyzed cyclization reaction of propargylic carbonates with carbon nucleophiles Org Lett 8 2006 5777 5780
16. L.-N. Guo, X.-H. Duan, H.-P. Bi, X.-Y. Liu, and Y.-M. Liang Palladium-catalyzed carboannulation of propargylic carbonates and nucleophiles to 2-substituted indenes J Org Chem 72 2007 1538 1540
17. H.-P. Bi, X.-Y. Liu, F.-R. Gou, L.-N. Guo, X.-H. Duan, and Y.-M. Liang Highly regioselective synthesis of indene derivatives including an allene functional group via Pd/C-catalyzed cyclization reaction in air Org Lett 9 2007 3527 3529
18. 3-propargylicpalladium complex J Org Chem 68 2003 8068 8074 (Pubitemid 37266563)
19. A. Okano, S. Oish, T. Tanaka, N. Fujii, and H. Ohno Construction of linked nitrogen heterocycles by palladium(0)-catalyzed intramolecular domino cyclization of 2-alkynylaziridines bearing a 2-aminoethyl group via ring expansion with isocyanate J Org Chem 75 2010 3396 3400
20. M. Yoshida, M. Fujita, T. Ishii, and M. Ihara A novel methodology for the synthesis of cyclic carbonates based on the palladium-catalyzed cascade reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, involving a novel carbon dioxide elimination-fixation process J Am Chem Soc 125 2003 4874 4881 (Pubitemid 36505380)
21. M. Yoshida, M. Higuchi, and K. Shishido Highly diastereoselective synthesis of tetrahydrobenzofuran derivatives by palladium-catalyzed reaction of propargylic esters with substituted β-dicarbonyl compounds Tetrahedron 66 2010 2675 2682
22. T. Takemura, K. Sugie, H. Nishino, S. Kawabata, and T. Koizumi Pd(0)-catalyzed polycondensation of methyl propargylic carbonate and bisphenols under stoichiometrically imbalanced conditions J Polym Sci Chem A: Polym Chem 46 2008 2250 2261 (Pubitemid 351363673)
23. T. Koizumi, K. Sugie, O. Kiyonaga, M. Yamanaka, and S. Kawabata Novel palladium-catalyzed polycondensation of propargyl carbonates and bisphenols. Synthesis of polyethers having exomethylene groups Macromolecules 37 2004 9670 9672 (Pubitemid 40079949)
24. N. Nishioka, and T. Koizumi Pd(0)-catalyzed polycondensation of aryl-substituted propargylic carbonates with bifunctional nucleophiles promoted by aryl group on the acetylenic terminal carbon J Polym Sci Chem A: Polym Chem 49 2011 642 649
25. E.J. Corey, and P.L. Fuchs A synthetic method for formyl → ethynyl conversion (RCHO → RCCH or RCCR′) Tetrahedron Lett 13 1972 3769 3772
26. J. Tsuji, K. Sato, and H. Okumoto Palladium-catalyzed decarboxylation-carbonylation of allylic carbonates to form. Β, γ-unsaturated esters J Org Chem 49 1984 1341 1344
27. M. Mori, K. Tonogaki, and A. Kinoshita Synthesis of 1,3-dienes from alkynes and ethylene: acetic acid 2-methylene-3-phenethylbut-3-enyl ester Org Synth 81 2005 1
28. K. Sonogashira, Y. Tohda, and N. Hagihara A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines Tetrahedron Lett 16 1975 4467 4470
29. W. Kurosawa, T. Kan, and T. Fukuyama Preparation of secondary amines from primary amines via 2-nitrobenzenesulfonamide: N-(4-methoxybenzyl)-3- phenylpropylamine Org Synth 79 2002 186