Au（Ⅰ）催化剂的负载及应用和FDU-NHC/Pd（Ⅱ）在偶联反应中的应用
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摘要
研发新型、高效的催化材料实现多相酸碱、金属以及不对称催化过程是目前和今后催化材料设计和催化反应研究领域的一个重要方向。
本论文分为两部分,第一部分是负载Au(Ⅰ)催化剂的制备、表征以及在Conia-Ene反应中的应用。金催化剂由于其独特的性质成为多相及均相过程中许多化学转化的一个最好选择,对于Au(Ⅰ)化合物的研究越来越引起人们的兴趣。Au(Ⅰ)化合物催化的加成反应以其反应条件温和、产品收率高等优点,在有机合成中占有重要一席,以膦为配体的Au(Ⅰ)催化的Conia-Ene加成反应便是其中的代表之一。传统Conia-Ene反应由于催化剂不可回收,产品易残留重金属等缺点,限制了其进一步发展,而将催化剂负载是解决传统Conia-Ene反应一系列缺点的有效途径。负载后的催化剂不仅具有反应条件适中、活性保持良好、贵金属消耗少等优点,而且可以循环利用,从而减少了对环境的污染,促进了绿色化学的发展。本论文首先将不同类型的材料(SBA-15、FDU、PEG-OMe)进行膦配体功能化,然后负载Au(Ⅰ)催化剂,从而制得几种不同的负载Au(Ⅰ)催化剂,并利用Conia-Ene反应考察催化性能。研究发现PEG/Au(Ⅰ)催化剂不仅对Conia-Ene反应具有较高的催化活性,而且可循环使用。反应体系已经进行了一部分的底物拓展,从分离收率方面来看和传统方法无异,下一步的底物拓展工作还在进行当中。
论文第二部分为FDU-15负载卡宾配体络合醋酸钯制备成多相钯催化剂FDU-NHC/Pd (Ⅱ),并应用于Sonogashira偶联反应和芳基硼酸化合物的自身偶联反应中。该催化剂对Sonogashira偶联反应不仅具有较高的催化活性,而且底物普适性很好,无论是对带有吸电子取代基还是供电子取代基的溴苯、碘苯都能够得到较好的分离产率(45-98%),并且催化剂可以循环使用10次；该催化剂对芳基硼酸化合物的自身偶联反应,也具有好的催化活性,最佳反应条件还在进-步优化当中。另外,通过运用XRD、N2吸附-脱附、TEM等手段对催化剂进行表征发现,功能化后的FDU-15比较好的保持了原来的结构。
The research of novel and efficient catalytic materials for heterogeneous acids and bases, metals and asymmetric catalytic process become one of the major investigations in the field of catalytic materials design and application.
This thesis was focused on two sections. In the first section, a series of supported Au (Ⅰ) catalysts were synthesized, characterized and applicated in Conia-Ene reaction. Gold catalysts, because of their unique properties, have now become a well-established best choice for many chemical transformations with pre-eminence established now in both heterogeneous and homogeneous processes. Gold-catalyzed reactions often proceed under mild conditions and obtain high yields in extremely small amounts so that they play an important role in organic synthetic chemistry. Phosphine ligands with Au (Ⅰ) catalyzed Conia-Ene addition reactions are one of the representatives. However, these traditional homogeneous catalysis processes often suffer several drawbacks, such as difficulties in recovering and recycling, an easy contamination of metal species in the reaction products, etc. The purposes to overcome these drawbacks have led to the immobilization of homogeneous Au catalysts. The supported catalysts light the pollution of environment and promote the development of green chemistry for the mild reaction conditions, good activity, low consumption of precious metals, especially the advantage of recycling. In this thesis, different types of materials (SBA-15, FDU, PEG-OMe) have been functionalized by phosphine ligands, and then mix with homogeneous Au (Ⅰ) catalysts, thus obtain several different supported Au (Ⅰ) catalysts. Their catalytic abilities were studied via Conia-Ene Reaction. The results indicated that the catalyst for the synthesis of DPC PEG/Au (Ⅰ) catalyst has high activity and recyclability. Further studies on the different substrates are in progress.
In the second section, we reported FDU-15-supported N-heterocyclic carbene-palladium catalyst (FDU-NHC/Pd (Ⅱ)) for Sonogashira coupling reaction and homocoupling of arylboronic acids. FDU-NHC/Pd (Ⅱ) was highly active for Sonogashira reactions of aryl halides and terminal alkynes. Both electron withdrawing and electron donor substrates could obtain the corresponding product with a satisfying yield (45-98%) and the catalyst could be reused 10 times. The catalyst also shows excellent activity in homocoupling of arylboronic acids, the choice of optimum conditions of work is in progress. In addition, FDU-NHC/Pd (Ⅱ) was characterized by XPS, XRD, N2 adsorption-desorption, and TEM, etc. Those results indicated that the catalyst well preserved the mesostructure after fictionalization.
本论文分为两部分,第一部分是负载Au(Ⅰ)催化剂的制备、表征以及在Conia-Ene反应中的应用。金催化剂由于其独特的性质成为多相及均相过程中许多化学转化的一个最好选择,对于Au(Ⅰ)化合物的研究越来越引起人们的兴趣。Au(Ⅰ)化合物催化的加成反应以其反应条件温和、产品收率高等优点,在有机合成中占有重要一席,以膦为配体的Au(Ⅰ)催化的Conia-Ene加成反应便是其中的代表之一。传统Conia-Ene反应由于催化剂不可回收,产品易残留重金属等缺点,限制了其进一步发展,而将催化剂负载是解决传统Conia-Ene反应一系列缺点的有效途径。负载后的催化剂不仅具有反应条件适中、活性保持良好、贵金属消耗少等优点,而且可以循环利用,从而减少了对环境的污染,促进了绿色化学的发展。本论文首先将不同类型的材料(SBA-15、FDU、PEG-OMe)进行膦配体功能化,然后负载Au(Ⅰ)催化剂,从而制得几种不同的负载Au(Ⅰ)催化剂,并利用Conia-Ene反应考察催化性能。研究发现PEG/Au(Ⅰ)催化剂不仅对Conia-Ene反应具有较高的催化活性,而且可循环使用。反应体系已经进行了一部分的底物拓展,从分离收率方面来看和传统方法无异,下一步的底物拓展工作还在进行当中。
论文第二部分为FDU-15负载卡宾配体络合醋酸钯制备成多相钯催化剂FDU-NHC/Pd (Ⅱ),并应用于Sonogashira偶联反应和芳基硼酸化合物的自身偶联反应中。该催化剂对Sonogashira偶联反应不仅具有较高的催化活性,而且底物普适性很好,无论是对带有吸电子取代基还是供电子取代基的溴苯、碘苯都能够得到较好的分离产率(45-98%),并且催化剂可以循环使用10次；该催化剂对芳基硼酸化合物的自身偶联反应,也具有好的催化活性,最佳反应条件还在进-步优化当中。另外,通过运用XRD、N2吸附-脱附、TEM等手段对催化剂进行表征发现,功能化后的FDU-15比较好的保持了原来的结构。
The research of novel and efficient catalytic materials for heterogeneous acids and bases, metals and asymmetric catalytic process become one of the major investigations in the field of catalytic materials design and application.
This thesis was focused on two sections. In the first section, a series of supported Au (Ⅰ) catalysts were synthesized, characterized and applicated in Conia-Ene reaction. Gold catalysts, because of their unique properties, have now become a well-established best choice for many chemical transformations with pre-eminence established now in both heterogeneous and homogeneous processes. Gold-catalyzed reactions often proceed under mild conditions and obtain high yields in extremely small amounts so that they play an important role in organic synthetic chemistry. Phosphine ligands with Au (Ⅰ) catalyzed Conia-Ene addition reactions are one of the representatives. However, these traditional homogeneous catalysis processes often suffer several drawbacks, such as difficulties in recovering and recycling, an easy contamination of metal species in the reaction products, etc. The purposes to overcome these drawbacks have led to the immobilization of homogeneous Au catalysts. The supported catalysts light the pollution of environment and promote the development of green chemistry for the mild reaction conditions, good activity, low consumption of precious metals, especially the advantage of recycling. In this thesis, different types of materials (SBA-15, FDU, PEG-OMe) have been functionalized by phosphine ligands, and then mix with homogeneous Au (Ⅰ) catalysts, thus obtain several different supported Au (Ⅰ) catalysts. Their catalytic abilities were studied via Conia-Ene Reaction. The results indicated that the catalyst for the synthesis of DPC PEG/Au (Ⅰ) catalyst has high activity and recyclability. Further studies on the different substrates are in progress.
In the second section, we reported FDU-15-supported N-heterocyclic carbene-palladium catalyst (FDU-NHC/Pd (Ⅱ)) for Sonogashira coupling reaction and homocoupling of arylboronic acids. FDU-NHC/Pd (Ⅱ) was highly active for Sonogashira reactions of aryl halides and terminal alkynes. Both electron withdrawing and electron donor substrates could obtain the corresponding product with a satisfying yield (45-98%) and the catalyst could be reused 10 times. The catalyst also shows excellent activity in homocoupling of arylboronic acids, the choice of optimum conditions of work is in progress. In addition, FDU-NHC/Pd (Ⅱ) was characterized by XPS, XRD, N2 adsorption-desorption, and TEM, etc. Those results indicated that the catalyst well preserved the mesostructure after fictionalization.
引文
[1]H. Huber, D. McIntosh, G. A. Ozin, Inorganic Chemistry,1977,16,975
[2]Z. Li, C. Brouwer, C. He, Chemical Reviews,2008,108,3239.
[3]A. Arcadi, Chemical Reviews,2008,108,3266.
[4]B. K. Min, C. M. Friend, Chemical Reviews,2007,107,2709.
[5]M.C. Daniel, D. Astruc, Chemical Reviews,2004,104,293.
[6]T. Ishida, M. Haruta, Angewandte Chemie International Edition,2007,46,7154.
[7]G. Bamwenda, S. Tsubota, T. Nakamura et al. Catalyst Letter,1997,44,83.
[8]A. Abad, P. Concepcion, A.Corma, H. Garcia, Angewandte Chemie International Edition,2005,44,4066.
[9]a) M. Okumura, S. Nakamura, S. Tsubota, T. Nakamura, M. Azuma, M. Haruta, Catalyst Letter,1998,51,53; b) M. Okumura, S. Tsubota, M. Haruta, Journal of Molecular Catalysis A:Chemical,2003,199,73.
[10]a) R. Zanella, L. Delannoy, C. Louis, Applied Catalysis A:General,2005,291,62; b) A. Mirescu, U. Priiβe, Applied Catalysis B:Environmental,2007,70,644; c) X. Zhang, H. Shi, B Xu, Angewandte Chemie International Edition,2005,44,7132. d) C. Baatz, U. Pruβe, Journal of Catalysis,2007,249,34.
[11]Y.C.Ma, F.Shi, Q.Y.Deng, Progress in Chemistry,2003,15,385.
[12]F. Shi, Q. Zhang, Y. Ma, Y. He, Y. Deng, Journal of the American Chemical Society,2005,127,4182.
[13](a) A.Corma, P.Serna, Nat. Protocol 2006,1,2590. (b) A. Corma,; P. Serna, Science,2006,313,332.
[14]A.Corma, P.Serna, H.Garcia, Journal of the American Chemical Society,2007, 129,6358.
[15]E. Taarning, A. T. Madsen, J. M. Marchetti, K. Egeblad, C. H. Christensen, Green Chemistry,2008,10,408.
[16]Y. Chang, D. J. H. Chen, Material,2009,165,664.
[17]H. Liu, Y. Liu, Y. Li, Z. Tang and H. Jiang, The Journal of Physical Chemistry C, 2010,114,13362.
[18]G.J. Hutchings, Journal of Catalysis,1985,96,292.
[19]S. Carrettin et al., Applied Catalysis A:General,2005,291,247.
[20]A. Corma, E. Gutierrez-Puebla, M. Iglesias, A. Monge, S. Perez-Ferreras and F. Sanchez, Advanced Synthesis & Catalysis,2006,348,1899.
[21]C. Gonzalez-Arellano, A. Abad, A. Corma, H. Garcia, M. Iglesias and F. Sanchez, Angewandte Chemie International Edition,2007,46,1536.
[22]Y. Miyazaki and S. Kobayashi, Journal of Combinatorial Chemistry,2008,10, 355.
[23]X. Zhang, F. X. Llabres i Xamena and A. Corma, Journal of Catalysis,2009,265, 155.
[24]M. Benaglia, A.Puglisi, F.Cozzi, Chemical Reviews,2003,103,3401.
[25]D. E.Bergbreiter, J. Top Li, Current Chemistry,2004,242,113.
[26]B. M. L. Dioos, I. F. J. Vankelecom and P. A. Jacobs, Advanced Synthesis & Catalysis,2006,348,1413.
[27]E. D. Bergbreiter, J. Tian and C. Hongfa, Chemical Reviews,2009,109,530.
[28]L Jinni and Patrick H. Toy, Chemical Reviews,2009,109,815.
[29]E. Bayer, V.Schurig, Angewandte Chemie International Edition in English,1975, 14,493.
[30]Y. Uozumi, M. Nakazono, Advanced Synthesis & Catalysis,2002,344,274.
[31]M. Benaglia, T. Danelli, F. Fabris, D. Sperandio, G. Pozzi, Organic Letters,2002, 4,4229.
[32]T. Danelli, R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi and G. Tocco, Tetrahedron:Asymmetry,2003,14,461.
[33]L. Wang, Y. Zhang, L. Liu, Y. Wang, The Journal of Organic Chemistry,2006, 71,1284.
[34]X.B. Wang, Y.G.Zhou, The Journal of Organic Chemistry,2008,73,5640.
[35]M. R.Luzung, J. P.Markham, F. D.Toste, Journal of the American Chemical Society,2004,126,10858.
[36]V. Mamane, T. Gress, H. Krause, Fuerstner, Journal of the American Chemical Society,2004,126,8654.
[37]L. Zhang, S.Kozmin, Journal of the American Chemical Society,2004,126, 11806.
[38]E. Mizushima, T. Hayashi, M.Tanaka, Organic Letters,2003,5,3349.
[39]D. J. Gorin, N. R.Davis, F. D.Toste, Journal of the American Chemical Society, 2005,127,11260.
[40]J. Zhang, C. G. Yang, C. He, Journal of the American Chemical Society,2006, 128,1798.
[41]Z. Li, J. Zhang, C. Brouwer, C. G. Yang, N. W. Reich, C. He, Organic Letters, 2006,8,4175.
[42]C. Y. Zhou, C. M. Che, Journal of the American Chemical Society,2007,129, 5828.
[43]S. M.Hi, L.P.Liu, Tang, Organic Letters,2006,8,4043.
[44]E. Genin, P. Y. Toullec, S. Antoniotti, C. Brancour, J. P. Genet, V. Michelet, Journal of the American Chemical Society,2006,128,3112.
[45]A. W. Sromek, M. Rubina, Gevorgyan, Journal of the American Chemical Society,2005,127,10500.
[46]A. C. H. M.mijs, L. V. Carrillo, A. M. Echavarren, Organic Letters,2007,9, 4021.
[47]G. Eglinton, M. C.Whiting, Journal of the Chemical Society,1953,3052.
[48]J. M. Conia, P.L.Perchec, Synthesis,1975,1,1.
[49]D. Caine, In ComprehensiVe; B. M.Trost, I. Eds. Fleming, Organic Synthesis, 1991,3,1.
[50]G. Fournet, G. Balme, B. Van Hemelryck, J. Gore, Tetrahedron Letters.1990,31, 5147.
[51]N. Monteiro, J. Gore, G. Balme, Tetrahedron 1992,48,10103.
[52]M. F. E. Donald, T. C. Olson, Tetrahedron Letters,1997,38,7691.
[53]P. Cruciani, C. Aubert, M. Malacria, Tetrahedron Letters,1994,35,6677
[54]O. Kitagawa, T. Suzuki, T. Inoue, Y. Watanabe, T. Taguchi, The Journal of Organic Chemistry,1998,63,9470.
[55]J. L. Renaud, M. Petit, C. Aubert, M. Malacria, Synlett 1997,931
[56]J. L. Renaud, C. Aubert, M. Malacria, Tetrahedron 1999,55,5113
[57]J. J. Kennedy-Smith, S. T. Staben, F. D. Toste, Journal of the American Chemical Society,2004,126,4526.
[58]S. T. Staben, J. J. Kennedy-Smith and F. D. Toste, Angewandte Chemie International Edition,2004,43,5350.
[59]P. J. Han, M Yang,G. Qao,N. N. Zhu,Y. D. Sang,Synthesis2007,6,2539.
[60]A. Ochida, H. Ito, M. Sawamura, Journal of the American Chemical Society, 2006,128,16486.
[61]H. Ito, Y. Makida, A. Ochida, H. Ohmiya, M. Sawamura, Organic Letters,2008, 10,5051.
[1]H.Diek, A.; Heck, F. R., Journal of Organometallic Chemistry,1975,93,295.
[2]L.Cassar, Journal of Organometallic Chemistry,1975,93,253.
[3]K. Sonogashira, Y. Tohda, Hagihara, N. Tetrahedron Letters.1975,16,4467.
[4]K. Sonogashira, Journal of Organometallic Chemistry,2002,653,46.
[5]E. Negishi, L. Anastasia, Chemical Reviews,2003,103,1979.
[6]R. Chinchilla, C. Najera, Chemical Reviews,2007,107,874.
[7]V. Polshettiwar, C. Len, A. Fihri, Coordination Chemistry Reviews,2009,253, 2599.
[8]L. Djakovitch, P. Rollet, Advanced Synthesis & Catalysis,2004,346,1782.
[9]M. Bandini, R. Luque, V. Budarin, D. Macquarrie, Tetrahedron,2005,61,9860.
[10]P. D. Stevens, G. Li, J. Fan, M. Yen, Y. Gao, Chemical Communications,2005, 4435.
[11]M. Cai, Q. Xu and P. Wang, Journal of Molecular Catalysis A:Chemical,2006, 250,199.
[12]P. H. Li, L. Wang, Advanced Synthesis & Catalysis,2006,348,681.
[13]J. H. Kim, D.H. Lee, B.H. Jun, Y.S. Lee, Tetrahedron Letters,2007,48,7079.
[14]M. Trilla, R. Pleixats, M. W. C. Man, C. Bied, J. J. E. Moreau, Advanced Synthesis & Catalysis,2008,350,577.
[15]J. Sedelmeier, S. V. Ley, H. Lange, I. R. Baxendale, European Journal of Organic Chemistry,2009,2009,4412.
[16]S. M. Islam, P. Mondal, A. S. Roy, S. Mondal, D. Hossain, Tetrahedron Letters, 2010,51,2067.
[17]G. Lee, H.K. Youn, M.J. Jin, W.J. Cheong, W.S. Ahn, Microporous and Mesoporous Materials,2010,132,232.
[18]T. Suzuka, Y. Okada, K. Ooshiro, Y. Uozumi, Tetrahedron,2010,66,1064.
[19]M. S. Wong, X. L. Zhang, Tetrahedron Letters,2001,42,4087.
[20]A. Lei, X. Zhang, Tetrahedron Letters,2002,43,2525.
[21]G. W. Kabalka, L. Wang, Tetrahedron Letters,2002,43,3067.
[22]J. P. Parrish et al, Tetrahedron Letters,2002,43,7899.
[23]H. Yoshida et al., Tetrahedron Letters,2003,44,1541.
[24]C. Gonzalez-Arellano, A. Corma, M. Iglesias, F. Sanchez, Chemical Communications,2005,1990.
[25]S. Carrettin, J. Guzman, A. Corma, Angewandte Chemie International Edition, 2005,44,2242.
[26]Y.Yamamoto, R. Suzuki, K. Hattori, H. Nishiyama,Synlett,2006,7,1027.
[27]C. Amatore, C. Cammoun, A. Jutand, European Journal of Organic Chemistry, 2008,2008,4567.
[28]J. S. Chen ET al., Journal of Molecular Catalysis A:Chemical,2008,285,14.
[29]T. Vogler, A. Studer, Advanced Synthesis & Catalysis,2008,350,1963.
[30]K. Mitsudo et al., Tetrahedron,2009,65,8384.
[31]Z. Jin, S. X. Guo, X. P. Gu, L. L. Qiu, H. B. Song, J. X. Fang, Advanced Synthesis & Catalysis,2009,351,1575.
[32]J. Mao, Q. Hua, G. Xie, Z. Yao, D. Shi, European Journal of Organic Chemistry, 2009,2009,2262.
[33]C.Yu, B.Tian, Z. Fan, G. D. Stucky, D. Zhao, Journal of the American Chemical Society,2002,124,4556.
[34]Y. Meng, D. Gu, F. Zhang, Y. Shi, H. Yang, Z Li, C.Yu, B.Tu, D. Zhao, Angewandte Chemie International Edition,2005,44,7053.
[35]F. Q. Zhang, Y. Meng, D. Gu, Y. Yan,; C. Yu, B. Tu, D. Zhao, Angewandte Chemie International Edition,2005,127,13508.
[36]Y. Meng, D. Gu, F. Zhang, Y. Shi, L. Cheng, D. Feng, Z. Wu, Z. Chen, Y. Wan, A. Stein, D. Zhao, Chemistry of Materials,2006,18,4447.
[37]F. Zhang, Y. Meng, D. Gu, Y. Yan, Z. Chen, B. Tu, D. Zhao, Chemistry of Materials,2006,18,5279.
[38]Y. Deng, T. Yu, Y. Wan, Y. Shi, Y. Meng, D. Gu, L. Zhang, Y. Huang, C. Liu, X. Wu, D. Zhao, Journal of the American Chemical Society,2007,129,1690.
[39]F. Zhang, D. Gu, T. Yu, F. Zhang, S. Xie, L. Zhang, Y. Deng, Y. Wan, B. Tu, D. Zhao, Journal of the American Chemical Society,2007,129,7746.
[40]R. Xing, N. Liu, Y. Liu, H. Wu, Y. Jiang, L. Chen, M. He, P. Wu, Advanced Functional Materials,2007,17,2455.
[41]S. Yan, Y. Gao, R. Xing, Y. Shen, Y. Liu, P. Wu, H. Wu, Tetrahedron,2008,64, 6294.
[42]R. Xing, Y. Liu, H. Wu, X. Li, M. He, P. Wu, Chemical Communications,2008, 6297.
[43]R. Xing, H. Wu, X. Li, Z. Zhao, Y. Liu, L. Chen, P. Wu, Journal of Materials Chemistry,2009,19,4004.
[44]C. Yao, H. Li, H. Wu, Y. Liu, P. Wu, Catalysis Communications,2009,10,1099.
[2]Z. Li, C. Brouwer, C. He, Chemical Reviews,2008,108,3239.
[3]A. Arcadi, Chemical Reviews,2008,108,3266.
[4]B. K. Min, C. M. Friend, Chemical Reviews,2007,107,2709.
[5]M.C. Daniel, D. Astruc, Chemical Reviews,2004,104,293.
[6]T. Ishida, M. Haruta, Angewandte Chemie International Edition,2007,46,7154.
[7]G. Bamwenda, S. Tsubota, T. Nakamura et al. Catalyst Letter,1997,44,83.
[8]A. Abad, P. Concepcion, A.Corma, H. Garcia, Angewandte Chemie International Edition,2005,44,4066.
[9]a) M. Okumura, S. Nakamura, S. Tsubota, T. Nakamura, M. Azuma, M. Haruta, Catalyst Letter,1998,51,53; b) M. Okumura, S. Tsubota, M. Haruta, Journal of Molecular Catalysis A:Chemical,2003,199,73.
[10]a) R. Zanella, L. Delannoy, C. Louis, Applied Catalysis A:General,2005,291,62; b) A. Mirescu, U. Priiβe, Applied Catalysis B:Environmental,2007,70,644; c) X. Zhang, H. Shi, B Xu, Angewandte Chemie International Edition,2005,44,7132. d) C. Baatz, U. Pruβe, Journal of Catalysis,2007,249,34.
[11]Y.C.Ma, F.Shi, Q.Y.Deng, Progress in Chemistry,2003,15,385.
[12]F. Shi, Q. Zhang, Y. Ma, Y. He, Y. Deng, Journal of the American Chemical Society,2005,127,4182.
[13](a) A.Corma, P.Serna, Nat. Protocol 2006,1,2590. (b) A. Corma,; P. Serna, Science,2006,313,332.
[14]A.Corma, P.Serna, H.Garcia, Journal of the American Chemical Society,2007, 129,6358.
[15]E. Taarning, A. T. Madsen, J. M. Marchetti, K. Egeblad, C. H. Christensen, Green Chemistry,2008,10,408.
[16]Y. Chang, D. J. H. Chen, Material,2009,165,664.
[17]H. Liu, Y. Liu, Y. Li, Z. Tang and H. Jiang, The Journal of Physical Chemistry C, 2010,114,13362.
[18]G.J. Hutchings, Journal of Catalysis,1985,96,292.
[19]S. Carrettin et al., Applied Catalysis A:General,2005,291,247.
[20]A. Corma, E. Gutierrez-Puebla, M. Iglesias, A. Monge, S. Perez-Ferreras and F. Sanchez, Advanced Synthesis & Catalysis,2006,348,1899.
[21]C. Gonzalez-Arellano, A. Abad, A. Corma, H. Garcia, M. Iglesias and F. Sanchez, Angewandte Chemie International Edition,2007,46,1536.
[22]Y. Miyazaki and S. Kobayashi, Journal of Combinatorial Chemistry,2008,10, 355.
[23]X. Zhang, F. X. Llabres i Xamena and A. Corma, Journal of Catalysis,2009,265, 155.
[24]M. Benaglia, A.Puglisi, F.Cozzi, Chemical Reviews,2003,103,3401.
[25]D. E.Bergbreiter, J. Top Li, Current Chemistry,2004,242,113.
[26]B. M. L. Dioos, I. F. J. Vankelecom and P. A. Jacobs, Advanced Synthesis & Catalysis,2006,348,1413.
[27]E. D. Bergbreiter, J. Tian and C. Hongfa, Chemical Reviews,2009,109,530.
[28]L Jinni and Patrick H. Toy, Chemical Reviews,2009,109,815.
[29]E. Bayer, V.Schurig, Angewandte Chemie International Edition in English,1975, 14,493.
[30]Y. Uozumi, M. Nakazono, Advanced Synthesis & Catalysis,2002,344,274.
[31]M. Benaglia, T. Danelli, F. Fabris, D. Sperandio, G. Pozzi, Organic Letters,2002, 4,4229.
[32]T. Danelli, R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi and G. Tocco, Tetrahedron:Asymmetry,2003,14,461.
[33]L. Wang, Y. Zhang, L. Liu, Y. Wang, The Journal of Organic Chemistry,2006, 71,1284.
[34]X.B. Wang, Y.G.Zhou, The Journal of Organic Chemistry,2008,73,5640.
[35]M. R.Luzung, J. P.Markham, F. D.Toste, Journal of the American Chemical Society,2004,126,10858.
[36]V. Mamane, T. Gress, H. Krause, Fuerstner, Journal of the American Chemical Society,2004,126,8654.
[37]L. Zhang, S.Kozmin, Journal of the American Chemical Society,2004,126, 11806.
[38]E. Mizushima, T. Hayashi, M.Tanaka, Organic Letters,2003,5,3349.
[39]D. J. Gorin, N. R.Davis, F. D.Toste, Journal of the American Chemical Society, 2005,127,11260.
[40]J. Zhang, C. G. Yang, C. He, Journal of the American Chemical Society,2006, 128,1798.
[41]Z. Li, J. Zhang, C. Brouwer, C. G. Yang, N. W. Reich, C. He, Organic Letters, 2006,8,4175.
[42]C. Y. Zhou, C. M. Che, Journal of the American Chemical Society,2007,129, 5828.
[43]S. M.Hi, L.P.Liu, Tang, Organic Letters,2006,8,4043.
[44]E. Genin, P. Y. Toullec, S. Antoniotti, C. Brancour, J. P. Genet, V. Michelet, Journal of the American Chemical Society,2006,128,3112.
[45]A. W. Sromek, M. Rubina, Gevorgyan, Journal of the American Chemical Society,2005,127,10500.
[46]A. C. H. M.mijs, L. V. Carrillo, A. M. Echavarren, Organic Letters,2007,9, 4021.
[47]G. Eglinton, M. C.Whiting, Journal of the Chemical Society,1953,3052.
[48]J. M. Conia, P.L.Perchec, Synthesis,1975,1,1.
[49]D. Caine, In ComprehensiVe; B. M.Trost, I. Eds. Fleming, Organic Synthesis, 1991,3,1.
[50]G. Fournet, G. Balme, B. Van Hemelryck, J. Gore, Tetrahedron Letters.1990,31, 5147.
[51]N. Monteiro, J. Gore, G. Balme, Tetrahedron 1992,48,10103.
[52]M. F. E. Donald, T. C. Olson, Tetrahedron Letters,1997,38,7691.
[53]P. Cruciani, C. Aubert, M. Malacria, Tetrahedron Letters,1994,35,6677
[54]O. Kitagawa, T. Suzuki, T. Inoue, Y. Watanabe, T. Taguchi, The Journal of Organic Chemistry,1998,63,9470.
[55]J. L. Renaud, M. Petit, C. Aubert, M. Malacria, Synlett 1997,931
[56]J. L. Renaud, C. Aubert, M. Malacria, Tetrahedron 1999,55,5113
[57]J. J. Kennedy-Smith, S. T. Staben, F. D. Toste, Journal of the American Chemical Society,2004,126,4526.
[58]S. T. Staben, J. J. Kennedy-Smith and F. D. Toste, Angewandte Chemie International Edition,2004,43,5350.
[59]P. J. Han, M Yang,G. Qao,N. N. Zhu,Y. D. Sang,Synthesis2007,6,2539.
[60]A. Ochida, H. Ito, M. Sawamura, Journal of the American Chemical Society, 2006,128,16486.
[61]H. Ito, Y. Makida, A. Ochida, H. Ohmiya, M. Sawamura, Organic Letters,2008, 10,5051.
[1]H.Diek, A.; Heck, F. R., Journal of Organometallic Chemistry,1975,93,295.
[2]L.Cassar, Journal of Organometallic Chemistry,1975,93,253.
[3]K. Sonogashira, Y. Tohda, Hagihara, N. Tetrahedron Letters.1975,16,4467.
[4]K. Sonogashira, Journal of Organometallic Chemistry,2002,653,46.
[5]E. Negishi, L. Anastasia, Chemical Reviews,2003,103,1979.
[6]R. Chinchilla, C. Najera, Chemical Reviews,2007,107,874.
[7]V. Polshettiwar, C. Len, A. Fihri, Coordination Chemistry Reviews,2009,253, 2599.
[8]L. Djakovitch, P. Rollet, Advanced Synthesis & Catalysis,2004,346,1782.
[9]M. Bandini, R. Luque, V. Budarin, D. Macquarrie, Tetrahedron,2005,61,9860.
[10]P. D. Stevens, G. Li, J. Fan, M. Yen, Y. Gao, Chemical Communications,2005, 4435.
[11]M. Cai, Q. Xu and P. Wang, Journal of Molecular Catalysis A:Chemical,2006, 250,199.
[12]P. H. Li, L. Wang, Advanced Synthesis & Catalysis,2006,348,681.
[13]J. H. Kim, D.H. Lee, B.H. Jun, Y.S. Lee, Tetrahedron Letters,2007,48,7079.
[14]M. Trilla, R. Pleixats, M. W. C. Man, C. Bied, J. J. E. Moreau, Advanced Synthesis & Catalysis,2008,350,577.
[15]J. Sedelmeier, S. V. Ley, H. Lange, I. R. Baxendale, European Journal of Organic Chemistry,2009,2009,4412.
[16]S. M. Islam, P. Mondal, A. S. Roy, S. Mondal, D. Hossain, Tetrahedron Letters, 2010,51,2067.
[17]G. Lee, H.K. Youn, M.J. Jin, W.J. Cheong, W.S. Ahn, Microporous and Mesoporous Materials,2010,132,232.
[18]T. Suzuka, Y. Okada, K. Ooshiro, Y. Uozumi, Tetrahedron,2010,66,1064.
[19]M. S. Wong, X. L. Zhang, Tetrahedron Letters,2001,42,4087.
[20]A. Lei, X. Zhang, Tetrahedron Letters,2002,43,2525.
[21]G. W. Kabalka, L. Wang, Tetrahedron Letters,2002,43,3067.
[22]J. P. Parrish et al, Tetrahedron Letters,2002,43,7899.
[23]H. Yoshida et al., Tetrahedron Letters,2003,44,1541.
[24]C. Gonzalez-Arellano, A. Corma, M. Iglesias, F. Sanchez, Chemical Communications,2005,1990.
[25]S. Carrettin, J. Guzman, A. Corma, Angewandte Chemie International Edition, 2005,44,2242.
[26]Y.Yamamoto, R. Suzuki, K. Hattori, H. Nishiyama,Synlett,2006,7,1027.
[27]C. Amatore, C. Cammoun, A. Jutand, European Journal of Organic Chemistry, 2008,2008,4567.
[28]J. S. Chen ET al., Journal of Molecular Catalysis A:Chemical,2008,285,14.
[29]T. Vogler, A. Studer, Advanced Synthesis & Catalysis,2008,350,1963.
[30]K. Mitsudo et al., Tetrahedron,2009,65,8384.
[31]Z. Jin, S. X. Guo, X. P. Gu, L. L. Qiu, H. B. Song, J. X. Fang, Advanced Synthesis & Catalysis,2009,351,1575.
[32]J. Mao, Q. Hua, G. Xie, Z. Yao, D. Shi, European Journal of Organic Chemistry, 2009,2009,2262.
[33]C.Yu, B.Tian, Z. Fan, G. D. Stucky, D. Zhao, Journal of the American Chemical Society,2002,124,4556.
[34]Y. Meng, D. Gu, F. Zhang, Y. Shi, H. Yang, Z Li, C.Yu, B.Tu, D. Zhao, Angewandte Chemie International Edition,2005,44,7053.
[35]F. Q. Zhang, Y. Meng, D. Gu, Y. Yan,; C. Yu, B. Tu, D. Zhao, Angewandte Chemie International Edition,2005,127,13508.
[36]Y. Meng, D. Gu, F. Zhang, Y. Shi, L. Cheng, D. Feng, Z. Wu, Z. Chen, Y. Wan, A. Stein, D. Zhao, Chemistry of Materials,2006,18,4447.
[37]F. Zhang, Y. Meng, D. Gu, Y. Yan, Z. Chen, B. Tu, D. Zhao, Chemistry of Materials,2006,18,5279.
[38]Y. Deng, T. Yu, Y. Wan, Y. Shi, Y. Meng, D. Gu, L. Zhang, Y. Huang, C. Liu, X. Wu, D. Zhao, Journal of the American Chemical Society,2007,129,1690.
[39]F. Zhang, D. Gu, T. Yu, F. Zhang, S. Xie, L. Zhang, Y. Deng, Y. Wan, B. Tu, D. Zhao, Journal of the American Chemical Society,2007,129,7746.
[40]R. Xing, N. Liu, Y. Liu, H. Wu, Y. Jiang, L. Chen, M. He, P. Wu, Advanced Functional Materials,2007,17,2455.
[41]S. Yan, Y. Gao, R. Xing, Y. Shen, Y. Liu, P. Wu, H. Wu, Tetrahedron,2008,64, 6294.
[42]R. Xing, Y. Liu, H. Wu, X. Li, M. He, P. Wu, Chemical Communications,2008, 6297.
[43]R. Xing, H. Wu, X. Li, Z. Zhao, Y. Liu, L. Chen, P. Wu, Journal of Materials Chemistry,2009,19,4004.
[44]C. Yao, H. Li, H. Wu, Y. Liu, P. Wu, Catalysis Communications,2009,10,1099.