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Palladium-Catalyzed Inter- and Intramolecular Coupling Reactions of Aryl and Vinyl Halides Mediated by Indium
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    Palladium-Catalyzed Inter- and Intramolecular Coupling Reactions of Aryl and Vinyl Halides Mediated by Indium
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    Department of Chemistry, Kangwon National University, Chunchon 200-701, Republic of Korea
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    Organic Letters

    Cite this: Org. Lett. 2005, 7, 2, 343–345
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    https://doi.org/10.1021/ol047567v
    Published December 23, 2004
    Copyright © 2005 American Chemical Society

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    Treatment of aryl and vinyl halides with 50 mol % of 100 mesh indium, 2.5 mol % of Pd−C, and 1.5 equiv of LiCl under mild conditions (DMF, 100 °C, 1−3 h) could produce coupling products efficiently in good to excellent yields in which the Csp2−Csp2 bond was formed. This reagent worked equally well with both intermolecular and intramolecular coupling reactions, producing a variety of biaryls, 1,3-dienes, and cyclic compounds.

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    9. Enrique Font-Sanchis,, F. Javier Céspedes-Guirao,, Ángela Sastre-Santos, and, Fernando Fernández-Lázaro. Indium-Mediated Synthesis of Heterobiaryls. The Journal of Organic Chemistry 2007, 72 (9) , 3589-3591. https://doi.org/10.1021/jo062638k
    10. Lunxiang Yin and, Jürgen Liebscher. Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts. Chemical Reviews 2007, 107 (1) , 133-173. https://doi.org/10.1021/cr0505674
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    23. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2017https://doi.org/10.1002/9780471264194.fos05791.pub6
    24. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2017https://doi.org/10.1002/9780471264194.fos05791.pub7
    25. . Zinc. 2017, 13-160. https://doi.org/10.1002/9781118929124.ch3
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    27. Gang Qi, Yunhai Yu, Junpo He. Synthesis of a [60]fullerene-end-capped polyacetylene derivative – a “rod-sphere” molecule from a “coil-sphere” precursor. Polymer Chemistry 2016, 7 (7) , 1461-1467. https://doi.org/10.1039/C5PY01674F
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    29. Killian Oukoloff, Frédéric Buron, Sylvain Routier, Ludovic Jean, Pierre‐Yves Renard. Synthetic Route to Rare Isoindolones Derivatives. European Journal of Organic Chemistry 2015, 2015 (11) , 2450-2456. https://doi.org/10.1002/ejoc.201403649
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    31. Yi-An Chen, Ching-Yuan Liu. Convenient synthesis of organic-electronics-oriented building blocks via on-water and under-air homocoupling of (hetero)aryl iodides. RSC Advances 2015, 5 (91) , 74180-74188. https://doi.org/10.1039/C5RA13517F
    32. David W. Manley, John C. Walton. A Clean and Selective Radical Homocoupling Employing Carboxylic Acids with Titania Photoredox Catalysis. Organic Letters 2014, 16 (20) , 5394-5397. https://doi.org/10.1021/ol502625w
    33. Xiuling Chen, Tieqiao Chen, Yuqiang Xiang, Yongbo Zhou, Daoqing Han, Li-Biao Han, Shuang-Feng Yin. Metal-free regioselective hydrobromination of alkynes through C H/C Br activation. Tetrahedron Letters 2014, 55 (33) , 4572-4575. https://doi.org/10.1016/j.tetlet.2014.06.070
    34. Christine Kallweit, Gebhard Haberhauer, Sascha Woitschetzki. 4,4′‐Bipyridine as a Unidirectional Switching Unit for a Molecular Pushing Motor. Chemistry – A European Journal 2014, 20 (21) , 6358-6365. https://doi.org/10.1002/chem.201304166
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    37. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2013, 275-276. https://doi.org/10.1002/9780471264194.fos05791.pub5
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    39. Huanfeng Jiang, Li He, Xianwei Li, Huoji Chen, Wanqing Wu, Wei Fu. Facile synthesis of dibranched conjugated dienes via palladium-catalyzed oxidative coupling of N-tosylhydrazones. Chemical Communications 2013, 49 (80) , 9218. https://doi.org/10.1039/c3cc43593h
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    42. Yiyuan Ding, Kai Cheng, Chenze Qi, Qingbao Song. Ferrous salt-promoted homocoupling of arenediazonium tetrafluoroborates under mild conditions. Tetrahedron Letters 2012, 53 (46) , 6269-6272. https://doi.org/10.1016/j.tetlet.2012.09.028
    43. Juntae Mo, Dahan Eom, Sung Hong Kim, Phil Ho Lee. Palladium-catalyzed Carbon–Sulfur Cross-coupling Reactions of Aryl Chlorides with Indium Tris(organothiolates). Chemistry Letters 2011, 40 (9) , 980-982. https://doi.org/10.1246/cl.2011.980
    44. Jun-Tae Mo, Hoon Hwang, Phil-Ho Lee. Palladium-Catalyzed Cross-Coupling Reaction and Gold-Catalyzed Cyclization for Preparation of Ethyl 2-Aryl 2,3-Alkadienoates and α-Aryl γ-Butenolides. Bulletin of the Korean Chemical Society 2011, 32 (spc8) , 2911-2915. https://doi.org/10.5012/bkcs.2011.32.8.2911
    45. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2011, 325-327. https://doi.org/10.1002/9780471264194.fos05791.pub4
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    47. Kooyeon Lee, Hyunseok Kim, Juntae Mo, Phil Ho Lee. Palladium‐Catalyzed Allyl Cross‐Coupling Reactions with In Situ Generated Organoindium Reagents. Chemistry – An Asian Journal 2011, 6 (8) , 2147-2157. https://doi.org/10.1002/asia.201000890
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    50. Linjun Shao, Yijun Du, Minfeng Zeng, Xiudong Li, Wenting Shen, Shufeng Zuo, Yueqing Lu, Xian‐Man Zhang, Chenze Qi. Ethanol‐promoted reductive homocoupling reactions of aryl halides catalyzed by palladium on carbon (Pd/C). Applied Organometallic Chemistry 2010, 24 (5) , 421-425. https://doi.org/10.1002/aoc.1635
    51. Seung-Hoi Kim, Reuben D. Rieke. 2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction. Tetrahedron 2010, 66 (17) , 3135-3146. https://doi.org/10.1016/j.tet.2010.02.061
    52. Tse-Lok Ho, Mary Fieser, Louis Fieser, Janice Smith. Phenyliodine(III) diacetate. 2010, 000-000. https://doi.org/10.1002/9780471264194.fos07981.pub3
    53. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2010, 000-000. https://doi.org/10.1002/9780471264194.fos05791.pub3
    54. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2009, 000-000. https://doi.org/10.1002/9780471264194.fos05791.pub2
    55. Shan-Yong Chen, Ji Zhang, Ying-Hao Li, Jun Wen, Shao-Quan Bian, Xiao-Qi Yu. Cobalt-catalyzed homo-coupling of aryl and alkenyl bromide using atmospheric oxygen as oxidant. Tetrahedron Letters 2009, 50 (49) , 6795-6797. https://doi.org/10.1016/j.tetlet.2009.09.092
    56. Aurélien Moncomble, Pascal Le Floch, Corinne Gosmini. Cobalt‐Catalyzed Formation of Symmetrical Biaryls and Its Mechanism. Chemistry – A European Journal 2009, 15 (19) , 4770-4774. https://doi.org/10.1002/chem.200900542
    57. Ming Yu, Ri-Yuan Tang, Jin-Heng Li. Synthesis of 6,7-dihydro-5H-dibenzo[c,e]azepines and biaryls by palladium-catalyzed Ullmann reaction. Tetrahedron 2009, 65 (17) , 3409-3416. https://doi.org/10.1016/j.tet.2009.02.040
    58. Lesley A. Schmid, Carl J. Lovely. 2-Iodocyclohexen-2-One. 2009https://doi.org/10.1002/047084289X.rn01016
    59. A. V. Vasil’ev. Alkenylation of aromatic compounds. Russian Journal of Organic Chemistry 2009, 45 (1) , 1-17. https://doi.org/10.1134/S1070428009010011
    60. Kooyeon Lee, Phil Ho Lee. Efficient homo-coupling reactions of heterocyclic aromatic bromides catalyzed by Pd(OAc)2 using indium. Tetrahedron Letters 2008, 49 (27) , 4302-4305. https://doi.org/10.1016/j.tetlet.2008.04.123
    61. M.A. Brimble, J.S. Gibson, J. Sperry. Pyrans and their Benzo Derivatives: Synthesis. 2008, 419-699. https://doi.org/10.1016/B978-008044992-0.00608-8
    62. Birgitte H. Kaae, Kasper Harpsøe, Jette S. Kastrup, Alberto Contreras Sanz, Darryl S. Pickering, Bjørn Metzler, Rasmus P. Clausen, Michael Gajhede, Per Sauerberg, Tommy Liljefors, Ulf Madsen. Structural Proof of a Dimeric Positive Modulator Bridging Two Identical AMPA Receptor-Binding Sites. Chemistry & Biology 2007, 14 (11) , 1294-1303. https://doi.org/10.1016/j.chembiol.2007.10.012
    63. Monique K. Robinson, Vasilina S. Kochurina, James M. Hanna. Palladium-catalyzed homocoupling of arenediazonium salts: an operationally simple synthesis of symmetrical biaryls. Tetrahedron Letters 2007, 48 (43) , 7687-7690. https://doi.org/10.1016/j.tetlet.2007.08.083
    64. Anne Brennführer, Helfried Neumann, Stefan Klaus, Thomas Riermeier, Juan Almena, Matthias Beller. Palladium/di-1-adamantyl-n-butylphosphine-catalyzed reductive carbonylation of aryl and vinyl halides. Tetrahedron 2007, 63 (27) , 6252-6258. https://doi.org/10.1016/j.tet.2007.02.043
    65. Dong Seomoon, Kooyeon Lee, Hyunseok Kim, Phil Ho Lee. Inter‐ and Intramolecular Palladium‐Catalyzed Allyl Cross‐Coupling Reactions Using Allylindium Generated In Situ from Allyl Acetates, Indium, and Indium Trichloride. Chemistry – A European Journal 2007, 13 (18) , 5197-5206. https://doi.org/10.1002/chem.200601338
    66. . Indium and Gallium-Mediated Addition Reactions. Bulletin of the Korean Chemical Society 2007, 17-28. https://doi.org/10.5012/bkcs.2007.28.1.017
    67. Anna Rosiak, Wolfgang Frey, Jens Christoffers. Synthesis of Tetrahydropyran‐4‐ones and Thiopyran‐4‐ones from Donor‐Substituted α‐Bromostyrene Derivatives. European Journal of Organic Chemistry 2006, 2006 (17) , 4044-4054. https://doi.org/10.1002/ejoc.200600372
    68. Takakazu Yamamoto, Takuma Yasuda, Kazuaki Kobayashi, Isao Yamaguchi, Take-aki Koizumi, Daisuke Ishii, Masaru Nakagawa, Yoshihiro Mashiko, Norihiro Shimizu. Utilization of Industrially Available 2,3-Dichloro-1,3-butadiene for Direct Synthesis of 2,3-Diaryl-1,3-butadienes. Bulletin of the Chemical Society of Japan 2006, 79 (3) , 498-500. https://doi.org/10.1246/bcsj.79.498
    69. Phil Ho Lee, Hyun Kim, Kooyeon Lee. Regioselective Addition Reactions of Propargyl Bromides to Carbonyl Compounds with Gallium Catalyzed by Indium. Advanced Synthesis & Catalysis 2005, 347 (9) , 1219-1222. https://doi.org/10.1002/adsc.200505046
    70. Phil Ho Lee, Dong Seomoon, Kooyeon Lee. Palladium‐Catalyzed Inter‐ and Intramolecular Coupling Reactions of Aryl and Vinyl Halides Mediated by Indium.. ChemInform 2005, 36 (20) https://doi.org/10.1002/chin.200520085
    71. . Pd-Catalyzed Substitution Reactions with Organoindium Reagents in situ Generated from Indium and Allyl or Propargyl Halides. Bulletin of the Korean Chemical Society 2005, 157-160. https://doi.org/10.5012/bkcs.2005.26.1.157
    72. Phil Ho Lee, Yunkiu Heo, Dong Seomoon, Sundae Kim, Kooyeon Lee. Regioselective allylgallation of terminal alkynes. Chemical Communications 2005, 53 (14) , 1874. https://doi.org/10.1039/b417975g

    Organic Letters

    Cite this: Org. Lett. 2005, 7, 2, 343–345
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol047567v
    Published December 23, 2004
    Copyright © 2005 American Chemical Society

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