메뉴 건너뛰기




Volumn 350, Issue 11-12, 2008, Pages 1841-1849

Palladium-catalyzed trimerizations of terminal arylalkynes: Synthesis of 1,3-diaryl-2-arylethynyl-1,3-butadienes

Author keywords

Alkynes; Cross coupling; Enynes; Hydroalkynylation; Palladium

Indexed keywords


EID: 53849090290     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800182     Document Type: Article
Times cited : (27)

References (95)
  • 1
    • 53849118099 scopus 로고    scopus 로고
    • Metal-Catalyzed Reactions of Alkynes. Part II. For Part I, see
    • Metal-Catalyzed Reactions of Alkynes. Part II. For Part I, see: Y.-T. Wu, K.-H. Huang, C.-C. Shin, T.-C. Wu, Chem. Eur. J. 2008, 14, 6697-6703.
    • (2008) Chem. Eur. J , vol.14 , pp. 6697-6703
    • Wu, Y.-T.1    Huang, K.-H.2    Shin, C.-C.3    Wu, T.-C.4
  • 18
    • 53849084682 scopus 로고    scopus 로고
    • More recently, two special protocols were reported. For Au(III)-catalyzed coupling, see: a) C. González-Arellano, A. Abad, A. Corma, H. García, M. Iglesias, F. SSnchez, Angew. Chem. 2007, 119, 1558;
    • More recently, two special protocols were reported. For Au(III)-catalyzed coupling, see: a) C. González-Arellano, A. Abad, A. Corma, H. García, M. Iglesias, F. SSnchez, Angew. Chem. 2007, 119, 1558;
  • 20
    • 33845346761 scopus 로고    scopus 로고
    • for homocoupling reactions of an alkynylmagnesium chloride, see: b
    • for homocoupling reactions of an alkynylmagnesium chloride, see: b) A. Krasovskiy, A. Tishkov, V. del Amo, H. Mayr, P. Knochel, Angew. Chem. 2006, 118, 5132;
    • (2006) Angew. Chem , vol.118 , pp. 5132
    • Krasovskiy, A.1    Tishkov, A.2    del Amo, V.3    Mayr, H.4    Knochel, P.5
  • 23
    • 84890619148 scopus 로고    scopus 로고
    • M. Fujiwara, I. Ojima, in: Modern Rhodium-Catalyzed Organic Reactions, (Ed. : P. A. Evans), Wiley-VCH, Weinheim, 2005, p 129;
    • b) M. Fujiwara, I. Ojima, in: Modern Rhodium-Catalyzed Organic Reactions, (Ed. : P. A. Evans), Wiley-VCH, Weinheim, 2005, p 129;
  • 27
    • 17444400363 scopus 로고    scopus 로고
    • Reviews, see: a, Ed, K. H. Dötz, Springer, Berlin
    • Reviews, see: a) Metal Carbenes in Organic Synthesis, (Ed.: K. H. Dötz), Springer, Berlin, 2004;
    • (2004) Metal Carbenes in Organic Synthesis
  • 31
    • 33847737113 scopus 로고    scopus 로고
    • Catalysis under rare-earth silylamides [non-regioselective]: a R. M. Gauvin, L. Delevoye, R. A. Hassan, J. Keldenich, A. Mortreux, Inorg. Chem. 2007, 46, 1062;
    • Catalysis under rare-earth silylamides [non-regioselective]: a) R. M. Gauvin, L. Delevoye, R. A. Hassan, J. Keldenich, A. Mortreux, Inorg. Chem. 2007, 46, 1062;
  • 32
    • 34250163523 scopus 로고    scopus 로고
    • Ru-catalyzed dimerization: b M. Bassetti, C. Pasquini, A. Raneri, D. Rosato, J. Org. Chem. 2007, 72, 4558;
    • Ru-catalyzed dimerization: b) M. Bassetti, C. Pasquini, A. Raneri, D. Rosato, J. Org. Chem. 2007, 72, 4558;
  • 33
    • 33645452006 scopus 로고    scopus 로고
    • Rh-catalyzed dimerization: c W. Weng, C. Guo, R. Celenligil-Cetin, B. M. Foxman, O. V. Ozerov, Chem. Commun. 2006, 197;
    • Rh-catalyzed dimerization: c) W. Weng, C. Guo, R. Celenligil-Cetin, B. M. Foxman, O. V. Ozerov, Chem. Commun. 2006, 197;
  • 35
    • 10044256639 scopus 로고    scopus 로고
    • [non-regioselective]: M. Schäfer, J. Wolf, H. Werner, Organometallics 2004, 23, 5713;
    • e) [non-regioselective]: M. Schäfer, J. Wolf, H. Werner, Organometallics 2004, 23, 5713;
  • 37
    • 33846611597 scopus 로고    scopus 로고
    • Ir-catalyzed dimerization: g R. Ghosh, X. Zhang, P. Achord, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, J. Am. Chem. Soc. 2007, 129, 853;
    • Ir-catalyzed dimerization: g) R. Ghosh, X. Zhang, P. Achord, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, J. Am. Chem. Soc. 2007, 129, 853;
  • 38
    • 0037169069 scopus 로고    scopus 로고
    • Pd-catalyzed dimerization: h C. Yang, S. P. Nolan, J. Org. Chem. 2002, 67, 591;
    • Pd-catalyzed dimerization: h) C. Yang, S. P. Nolan, J. Org. Chem. 2002, 67, 591;
  • 40
    • 0037419829 scopus 로고    scopus 로고
    • Catalysis under rare-earth silylamides: a M. Nishiura, Z. Hou, Y. Wakatsuki, T. Yamaki, T. Miyamoto, J. Am. Chem. Soc. 2003, 125, 1184;
    • Catalysis under rare-earth silylamides: a) M. Nishiura, Z. Hou, Y. Wakatsuki, T. Yamaki, T. Miyamoto, J. Am. Chem. Soc. 2003, 125, 1184;
  • 42
    • 24944453067 scopus 로고    scopus 로고
    • Ru-catalyzed dimerization: c X. Chen, P. Xue, H. H. Y. Sung, I. D. Williams, M. Peruzzini, C. Bianchini, G. Jia, Organometallics 2005, 24, 4330;
    • Ru-catalyzed dimerization: c) X. Chen, P. Xue, H. H. Y. Sung, I. D. Williams, M. Peruzzini, C. Bianchini, G. Jia, Organometallics 2005, 24, 4330;
  • 46
    • 20444471183 scopus 로고    scopus 로고
    • Ir-catalyzed dimerization: g M. V. Jimínez, E. Sola, F. J. Lahoz, L. A. Oro, Organometallics 2005, 24, 2722.
    • Ir-catalyzed dimerization: g) M. V. Jimínez, E. Sola, F. J. Lahoz, L. A. Oro, Organometallics 2005, 24, 2722.
  • 47
    • 0000391747 scopus 로고    scopus 로고
    • Methylalumoxane-catalyzed dimerization: a A. K. Dash, M. S. Eisen, Org. Lett. 2000, 2, 737;
    • Methylalumoxane-catalyzed dimerization: a) A. K. Dash, M. S. Eisen, Org. Lett. 2000, 2, 737;
  • 48
    • 2542437885 scopus 로고    scopus 로고
    • catalysis under rare-earth silylamides: b K. Komeyama, K. Takehira, K. Takaki, Synthesis 2004, 1062;
    • catalysis under rare-earth silylamides: b) K. Komeyama, K. Takehira, K. Takaki, Synthesis 2004, 1062;
  • 49
    • 0033804837 scopus 로고    scopus 로고
    • Pd-catalyzed dimerizations: c U. Lücking, A. Pfaltz, Synlett 2000, 1261;
    • Pd-catalyzed dimerizations: c) U. Lücking, A. Pfaltz, Synlett 2000, 1261;
  • 57
    • 0033610479 scopus 로고    scopus 로고
    • by Pd complexes, see: d J. Krause, G. Cestaric, K.-J. Haack, K. Seevogel, W. Storm, K.-R. Pörschke, J. Am. Chem. Soc. 1999, 121, 9807;
    • by Pd complexes, see: d) J. Krause, G. Cestaric, K.-J. Haack, K. Seevogel, W. Storm, K.-R. Pörschke, J. Am. Chem. Soc. 1999, 121, 9807;
  • 58
    • 37049088478 scopus 로고    scopus 로고
    • by zirconocenes: e A. D. Horton, J. Chem. Soc. Chem. Commun. 1992, 185.
    • by zirconocenes: e) A. D. Horton, J. Chem. Soc. Chem. Commun. 1992, 185.
  • 59
    • 53849086708 scopus 로고    scopus 로고
    • Trimerization catalyzed by diiridium complexes, see: ref, 13g
    • [13g].
  • 60
    • 53849090862 scopus 로고    scopus 로고
    • GC analysis cannot provide accurate information for determination of the products because compound Z-7a generates one unknown product at ca. 250 °C
    • GC analysis cannot provide accurate information for determination of the products because compound Z-7a generates one unknown product at ca. 250 °C.
  • 61
    • 53849113869 scopus 로고    scopus 로고
    • Although it is well reported that copper(I) acetylides are important reagents or intermediates for preparations of alkynyl derivatives, σ-alkynyl Pd complexes generated from terminal arylalkynes and Pd(0) catalysts can also exhibit a similar function. There are several examples for copper-free alkyne homocouplings (ref.[8, copper-free synthesis of enynes 6 (refs.[14d,e, and the copper-free Sonogarshira reactions, see: a) H. Kawanami, K. Matsushima, M. Sato, Y. Ikushima, Angew. Chem. 2007, 119, 5221;
    • [14d,e]) and the copper-free Sonogarshira reactions, see: a) H. Kawanami, K. Matsushima, M. Sato, Y. Ikushima, Angew. Chem. 2007, 119, 5221;
  • 75
    • 53849144524 scopus 로고    scopus 로고
    • Compound Z-7d: C27H24, monoclinic crystals of space group C2/c, unit cell dimensions: a=18.673(3, b= 6.1099(9, c=36.375(6) Å, α=90, β=100.215(3, γ= 90°, V=4084.2(10) Å3, Z=8, Crystal size: 0.30×0.23× 0.10 mm3. Compound Z-7o: C48H30, triclinic crystals of space group P1, unit cell dimensions: a=9.0868(18, b=13.068(2, c=15.152(3) Å, α=65.804(8, β=80.282(8, γ=85.118(8)°, V=1617.4(5) Å3, Z=2, Crystal size: 0.10×0.10×0.04 mm3. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC 672448 (Z-7d) and 671872 (Z-7o) contain the supplementary cryst
    • 3. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. CCDC 672448 (Z-7d) and 671872 (Z-7o) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif or on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk].
  • 76
    • 25144451317 scopus 로고    scopus 로고
    • 1H NMR spectra of these two regioisomers are very similar to those of their analogues, (3E/3Z)-2-butyl-3-(1-hexynyl)deca-1,3-diene, see: M. Kim, R. L. Miller, D. Lee, J. Am. Chem. Soc. 2005, 127, 12818.
    • 1H NMR spectra of these two regioisomers are very similar to those of their analogues, (3E/3Z)-2-butyl-3-(1-hexynyl)deca-1,3-diene, see: M. Kim, R. L. Miller, D. Lee, J. Am. Chem. Soc. 2005, 127, 12818.
  • 77
    • 53849111802 scopus 로고    scopus 로고
    • In these control experiments, only the reaction products of type 10 were isolated and characterized. Self-dimerization and -trimerization adducts of alkynes 4 and traces of other regioisomers were also formed but neglected
    • In these control experiments, only the reaction products of type 10 were isolated and characterized. Self-dimerization and -trimerization adducts of alkynes 4 and traces of other regioisomers were also formed but neglected.
  • 78
    • 53849115982 scopus 로고    scopus 로고
    • 9c was heated at 80 °C for 1 d in our catalytic system, a complex mixture was generated and only ca
    • When enyne 9c was heated at 80 °C for 1 d in our catalytic system, a complex mixture was generated and only ca. 30% of the starting material was recovered.
    • 30% of the starting material was recovered
    • When enyne1
  • 79
    • 53849141719 scopus 로고    scopus 로고
    • 2 atmosphere for 1 d without obvious decomposition. Attempts at the preparation of a tetramer from the reaction of Z-7a and 4a with our protocol were also not successful.
    • 2 atmosphere for 1 d without obvious decomposition. Attempts at the preparation of a tetramer from the reaction of Z-7a and 4a with our protocol were also not successful.
  • 80
    • 53849124913 scopus 로고    scopus 로고
    • 2 and 4, or by the transmetallation from the corresponding copper(I) acetylide.
    • 2 and 4, or by the transmetallation from the corresponding copper(I) acetylide.
  • 81
    • 53849091932 scopus 로고    scopus 로고
    • [14d]
    • [14d]
  • 82
    • 53849128398 scopus 로고    scopus 로고
    • Dienynes Z-7 can be formulated to have a skeleton of 1,3-hexadien-5-yne. It has been reported that 1,3-hexadien-5-yne can generate benzene via isobenzenediyne, see: H. Hopf, H. Berger, G. Zimmermann, U. Nüchter, P. G. Jones, I. Dix, Angew. Chem. 1997, 109, 1236;
    • Dienynes Z-7 can be formulated to have a skeleton of 1,3-hexadien-5-yne. It has been reported that 1,3-hexadien-5-yne can generate benzene via isobenzenediyne, see: H. Hopf, H. Berger, G. Zimmermann, U. Nüchter, P. G. Jones, I. Dix, Angew. Chem. 1997, 109, 1236;
  • 84
    • 53849094310 scopus 로고    scopus 로고
    • 3.
    • 3.
  • 85
    • 53849133668 scopus 로고    scopus 로고
    • 6π-Electrocyclization: a O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285;
    • 6π-Electrocyclization: a) O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.