Palladium-Catalyzed Inter- and Intramolecular Coupling Reactions of Aryl and Vinyl Halides Mediated by IndiumClick to copy article linkArticle link copied!
Abstract
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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(17)
, 12224-12235. https://doi.org/10.1021/acs.joc.3c00567
- Guo-Lin Gao, Wujiong Xia, Pankaj Jain, and Jin-Quan Yu . Pd(II)-Catalyzed C3-Selective Arylation of Pyridine with (Hetero)arenes. Organic Letters 2016, 18
(4)
, 744-747. https://doi.org/10.1021/acs.orglett.5b03712
- Sanghyuck Kim, Cheol-Eui Kim, Boram Seo, and Phil Ho Lee . In Situ Generation of Phosphoryl Alkylindiums and Their Synthetic Application to Arylalkyl Phosphonates via Palladium-Catalyzed Cross-Coupling Reactions. Organic Letters 2014, 16
(21)
, 5552-5555. https://doi.org/10.1021/ol502540z
- Yu Peng, Long Luo, Chang-Song Yan, Jian-Jian Zhang, and Ya-Wen Wang . Ni-Catalyzed Reductive Homocoupling of Unactivated Alkyl Bromides at Room Temperature and Its Synthetic Application. The Journal of Organic Chemistry 2013, 78
(21)
, 10960-10967. https://doi.org/10.1021/jo401936v
- Zhi-Liang Shen, Shun-Yi Wang, Yew-Keong Chok, Yun-He Xu, and Teck-Peng Loh . Organoindium Reagents: The Preparation and Application in Organic Synthesis. Chemical Reviews 2013, 113
(1)
, 271-401. https://doi.org/10.1021/cr300051y
- Dahan Eom, Sangjune Park, Youngchul Park, Taekyu Ryu, and Phil Ho Lee . Synthesis of Indenes via Brønsted Acid Catalyzed Cyclization of Diaryl- and Alkyl Aryl-1,3-dienes. Organic Letters 2012, 14
(21)
, 5392-5395. https://doi.org/10.1021/ol302271w
- Phil Ho Lee, Youngchul Park, Sangkyun Park, Euijae Lee, and Sunggak Kim . Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure. The Journal of Organic Chemistry 2011, 76
(3)
, 760-765. https://doi.org/10.1021/jo102441t
- Phil Ho Lee, Juntae Mo, Dongjin Kang, Dahan Eom, Chansoo Park, Chang-Hee Lee, Young Mee Jung, and Hyonseok Hwang. Preparation of Ethyl 2-Aryl 2,3-Alkadienoates via Palladium-Catalyzed Selective Cross-Coupling Reactions. The Journal of Organic Chemistry 2011, 76
(1)
, 312-315. https://doi.org/10.1021/jo1020085
- 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
- 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
- José Barluenga,, Patricia Moriel,, Fernando Aznar, and, Carlos Valdés. Palladium-Catalyzed Cross-Coupling between Vinyl Halides and tert-Butyl Carbazate: First General Synthesis of the Unusual N-Boc-N-alkenylhydrazines. Organic Letters 2007, 9
(2)
, 275-278. https://doi.org/10.1021/ol062726r
- Phil Ho Lee,, Kooyeon Lee, and, Youngjin Kang. In Situ Generation of Vinyl Allenes and Its Applications to One-Pot Assembly of Cyclohexene, Cyclooctadiene, 3,7-Nonadienone, and Bicyclo[6.4.0]dodecene Derivatives with Palladium-Catalyzed Multicomponent Reactions. Journal of the American Chemical Society 2006, 128
(4)
, 1139-1146. https://doi.org/10.1021/ja054144v
- Dalong Shen, Dehai Cao, Ruizeng Zhang, Peiyuan Bai, Zhenxing Liu. Lewis acid catalyzed Markovnikov hydrobromination and hydrochlorination of alkynes using TMSX (X = Br, Cl). Organic & Biomolecular Chemistry 2024, 22
(20)
, 4062-4066. https://doi.org/10.1039/D4OB00608A
- Damodar J. Sutar, Sunil N. Zende, Pradeep M. Mhaldar, Dattaprasad M. Pore, Asmita S. Tapase, Gavisiddappa S. Gokavi. Reductive Ullmann-Type Homocoupling of Aryl Halides Catalysed by Mixed Metal Oxide Nanocomposite (Pd/MnFe2O4) Under Aqueous Condition. Catalysis Letters 2024, 154
(3)
, 1209-1218. https://doi.org/10.1007/s10562-023-04378-z
- Gokanapalli Anusha, Meeniga Indira, Irla Siva Kumar, Loka Subramanyam Sarma, Kakarla Raghava Reddy, Peddiahgari Vasu Govardhana Reddy, Tejraj M. Aminabhavi. Synthesis of bis-1,3-(benz)azoles catalyzed by palladium-PEPPSI complex-based catalysts and the study of photophysical properties. Chemosphere 2022, 301 , 134751. https://doi.org/10.1016/j.chemosphere.2022.134751
- Hongyu Guo, Sheng Zhang, Yang Li, Xiaoqiang Yu, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao. Palladium‐Catalyzed Tail‐to‐Tail Reductive Dimerization of Terminal Alkynes to 2,3‐Dibranched Butadienes. Angewandte Chemie International Edition 2022, 61
(13)
https://doi.org/10.1002/anie.202116870
- Hongyu Guo, Sheng Zhang, Yang Li, Xiaoqiang Yu, Xiujuan Feng, Yoshinori Yamamoto, Ming Bao. Palladium‐Catalyzed Tail‐to‐Tail Reductive Dimerization of Terminal Alkynes to 2,3‐Dibranched Butadienes. Angewandte Chemie 2022, 134
(13)
https://doi.org/10.1002/ange.202116870
- Ramuel John Inductivo Tamargo, Peter Yuosef M. Rubio, Sonaimuthu Mohandoss, Jae‐Jin Shim, Yong Rok Lee. Cyrene™ as a Neoteric Bio‐Based Solvent for Catalyst‐Free Microwave‐Assisted Construction of Diverse Bipyridine Analogues for Heavy‐Metal Sensing. ChemSusChem 2021, 14
(9)
, 2133-2140. https://doi.org/10.1002/cssc.202100379
- Xiang Liu, Didier Astruc. Development of the Applications of Palladium on Charcoal in Organic Synthesis. Advanced Synthesis & Catalysis 2018, 360
(18)
, 3426-3459. https://doi.org/10.1002/adsc.201800343
- Richard C. Larock, Xiaoxia Zhang. Formation of Alkanes and Arenes by Coupling Reactions. 2018, 1-149. https://doi.org/10.1002/9781118662083.cot01-002
- Meriem Abderrezak, Zahia Kabouche, Christian Bruneau, Cédric Fischmeister. Ene-yne Cross-Metathesis for the Preparation of 2,3-Diaryl-1,3-dienes. Catalysts 2017, 7
(12)
, 365. https://doi.org/10.3390/catal7120365
- Yunhai Yu, Junpo He. Anionic Polymerizations of Bis(terphenyl) Substituted Butadienes for Precursors of Head‐to‐Head Substituted Polyacetylenes. Macromolecular Chemistry and Physics 2017, 218
(12)
https://doi.org/10.1002/macp.201700080
- Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2017https://doi.org/10.1002/9780471264194.fos05791.pub6
- Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2017https://doi.org/10.1002/9780471264194.fos05791.pub7
- . Zinc. 2017, 13-160. https://doi.org/10.1002/9781118929124.ch3
- Mario A. Macías, Enrique Pandolfi, Valeria Schapiro, Gustavo P. Silveira, Guilherme D. Vilela, Leopoldo Suescun. Crystal structure and absolute configuration of (3a
R
,3′a
R
,7a
S
,7′a
S
)-2,2,2′,2′-tetramethyl-3a,6,7,7a,3′a,6′,7′,7′a-octahydro-4,4′-bi[1,3-benzodioxolyl], obtained from a Pd-catalyzed homocoupling reaction. Acta Crystallographica Section E Crystallographic Communications 2017, 73
(1)
, 81-84. https://doi.org/10.1107/S2056989016019927
- 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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(13)
, 2868-2878. https://doi.org/10.1002/ejoc.201500248
- 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
- Woo Hyung Jeon, Hyunseok Kim, Jang‐Sik Choi, Kooyeon Lee, Phil Ho Lee. Palladium‐catalyzed Intramolecular Coupling Reactions between Vinyl Bromides, Aryl and Vinyl Halides, and Aryl Iodides Mediated by Indium: Preparation of Five‐ to Eight‐membered Carbocycles and Heterocycles. Bulletin of the Korean Chemical Society 2015, 36
(2)
, 711-714. https://doi.org/10.1002/bkcs.10106
- 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
- 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
- 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
- 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
- Jiayi Wang, Yuan Li, Pinzhen Li, Gonghua Song. Polymerized functional ionic liquid supported Pd nanoparticle catalyst for reductive homocoupling of aryl halides. Monatshefte für Chemie - Chemical Monthly 2013, 144
(8)
, 1159-1163. https://doi.org/10.1007/s00706-013-0925-7
- Ueon Sang Shin, Kyung-Hwan Cho, Seung-Hoi Kim. Preparation 2-Substituted-4-pyridylzinc Bromides via Direct Insertion of Active Zinc and Their Coupling Reactions. Bulletin of the Korean Chemical Society 2013, 34
(5)
, 1575-1578. https://doi.org/10.5012/bkcs.2013.34.5.1575
- Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2013, 275-276. https://doi.org/10.1002/9780471264194.fos05791.pub5
- Gebhard Haberhauer, Christina Tepper, Christoph Wölper, Dieter Bläser. Tropos
, Nevertheless Conformationally Stable Biphenyl Derivatives. European Journal of Organic Chemistry 2013, 2013
(12)
, 2325-2333. https://doi.org/10.1002/ejoc.201300087
- 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
- Lauren M. Strawsine, Mohammad S. Mubarak, Dennis G. Peters. Use of Silver Cathodes to Promote the Direct Reduction and Intramolecular Cyclization of ω-Halo-1-phenyl-1-alkynes in Dimethylformamide. Journal of The Electrochemical Society 2013, 160
(7)
, G3030-G3037. https://doi.org/10.1149/2.007307jes
- Sungmin Lee, Seungwook Ji, Youngjong Kang. Synthesis and Characterizations of Bis-Spiropyran Derivatives. Bulletin of the Korean Chemical Society 2012, 33
(11)
, 3740-3744. https://doi.org/10.5012/bkcs.2012.33.11.3740
- 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
- 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
- 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
- Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2011, 325-327. https://doi.org/10.1002/9780471264194.fos05791.pub4
- Bo Ram Park, Ko Hoon Kim, Taek Hyeon Kim, Jae Nyoung Kim. Palladium-catalyzed benzoin-mediated redox process leading to biaryls from aryl halides. Tetrahedron Letters 2011, 52
(34)
, 4405-4407. https://doi.org/10.1016/j.tetlet.2011.06.045
- 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
- Subin Choi, Hoon Hwang, Phil Ho Lee. An Effective Diels–Alder Reaction of Vinyl Allenols with Dienophiles. European Journal of Organic Chemistry 2011, 2011
(7)
, 1351-1356. https://doi.org/10.1002/ejoc.201001148
- Seung-Hoi Kim, Reuben D. Rieke. Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis. Molecules 2010, 15
(11)
, 8006-8038. https://doi.org/10.3390/molecules15118006
- 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
- 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
- Tse-Lok Ho, Mary Fieser, Louis Fieser, Janice Smith. Phenyliodine(III) diacetate. 2010, 000-000. https://doi.org/10.1002/9780471264194.fos07981.pub3
- Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2010, 000-000. https://doi.org/10.1002/9780471264194.fos05791.pub3
- Tse‐Lok Ho, Mary Fieser, Louis Fieser. Indium. 2009, 000-000. https://doi.org/10.1002/9780471264194.fos05791.pub2
- 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
- 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
- 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
- Lesley A. Schmid, Carl J. Lovely. 2-Iodocyclohexen-2-One. 2009https://doi.org/10.1002/047084289X.rn01016
- A. V. Vasil’ev. Alkenylation of aromatic compounds. Russian Journal of Organic Chemistry 2009, 45
(1)
, 1-17. https://doi.org/10.1134/S1070428009010011
- 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
- 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
- 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
- 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
- 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
- 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
- . 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
- 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
- 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
- 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
- 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
- . 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
- 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
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