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Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic Azides

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    Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic Azides
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    Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, and Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2005, 127, 46, 15998–15999
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    https://doi.org/10.1021/ja054114s
    Published October 28, 2005
    Copyright © 2005 American Chemical Society
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    Abstract

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    Cp*RuCl(PPh3)2 is an effective catalyst for the regioselective “fusion” of organic azides and terminal alkynes, producing 1,5-disubstituted 1,2,3-triazoles. Internal alkynes also participate in this catalysis, resulting in fully substituted 1,2,3-triazoles.

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     The Hong Kong University of Science and Technology.

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     The Scripps Research Institute.

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    Experimental procedures and characterization data (PDF). X-ray crystallographic files (CIF). This material is available free of charge via the Internet at http://pubs.acs.org.

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    48. Miguel A. Sierra, María C. de la Torre. 1,2,3-Triazolium-Derived Mesoionic Carbene Ligands Bearing Chiral Sulfur-Based Moieties: Synthesis, Catalytic Properties, and Their Role in Chirality Transfer. ACS Omega 2019, 4 (8) , 12983-12994. https://doi.org/10.1021/acsomega.9b01285
    49. Sangeetha Donikela, Prathama S. Mainkar, Kiranmai Nayani, Srivari Chandrasekhar. Metal Free Domino β-Azidation/[3 + 2] Cycloaddition Reaction for the Synthesis of 1,2,3-Triazole-Fused Dihydrobenzoxazinones. The Journal of Organic Chemistry 2019, 84 (16) , 10546-10553. https://doi.org/10.1021/acs.joc.9b01660
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    67. Jens Engel-Andreasen, Isabelle Wellhöfer, Kathrine Wich, and Christian A. Olsen . Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates. The Journal of Organic Chemistry 2017, 82 (21) , 11613-11619. https://doi.org/10.1021/acs.joc.7b01744
    68. Yun Liao, Qianqian Lu, Gui Chen, Yinghua Yu, Chunsen Li, and Xueliang Huang . Rhodium-Catalyzed Azide–Alkyne Cycloaddition of Internal Ynamides: Regioselective Assembly of 5-Amino-Triazoles under Mild Conditions. ACS Catalysis 2017, 7 (11) , 7529-7534. https://doi.org/10.1021/acscatal.7b02558
    69. Woo Gyum Kim, Mi Eun Kang, Jae Bin Lee, Min Ho Jeon, Sungmin Lee, Jungha Lee, Bongseo Choi, Pedro M. S. D. Cal, Sebyung Kang, Jung-Min Kee, Gonçalo J. L. Bernardes, Jan-Uwe Rohde, Wonyoung Choe, and Sung You Hong . Nickel-Catalyzed Azide–Alkyne Cycloaddition To Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water. Journal of the American Chemical Society 2017, 139 (35) , 12121-12124. https://doi.org/10.1021/jacs.7b06338
    70. Xiang Fei, Megan E. Zavorka, Guillaume Malik, Christopher M. Connelly, Richard G. MacDonald, and David B. Berkowitz . General Linker Diversification Approach to Bivalent Ligand Assembly: Generation of an Array of Ligands for the Cation-Independent Mannose 6-Phosphate Receptor. Organic Letters 2017, 19 (16) , 4267-4270. https://doi.org/10.1021/acs.orglett.7b01914
    71. Xavier Creary, Kyle Chormanski, Gabriel Peirats, and Carol Renneburg . Electronic Properties of Triazoles. Experimental and Computational Determination of Carbocation and Radical-Stabilizing Properties. The Journal of Organic Chemistry 2017, 82 (11) , 5720-5730. https://doi.org/10.1021/acs.joc.7b00548
    72. Kelvin Pak Shing Cheung and Gavin Chit Tsui . Copper(I)-Catalyzed Interrupted Click Reaction with TMSCF3: Synthesis of 5-Trifluoromethyl 1,2,3-Triazoles. Organic Letters 2017, 19 (11) , 2881-2884. https://doi.org/10.1021/acs.orglett.7b01116
    73. Kai Huang, Guorong Sheng, Ping Lu, and Yanguang Wang . From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles. The Journal of Organic Chemistry 2017, 82 (10) , 5294-5300. https://doi.org/10.1021/acs.joc.7b00627
    74. Ajay Gupta, Ramen Jamatia, Mrityunjoy Mahato, and Amarta Kumar Pal . Metalloprotein-Inspired Ruthenium Polymeric Complex: A Highly Efficient Catalyst in Parts per Million Level for 1,3-Dipolar Huisgen’s Reaction in Aqueous Medium at Room Temperature. Industrial & Engineering Chemistry Research 2017, 56 (9) , 2375-2382. https://doi.org/10.1021/acs.iecr.6b04863
    75. Wenjun Li, Manjaly J. Ajitha, Ming Lang, Kuo-Wei Huang, and Jian Wang . Catalytic Intermolecular Cross-Couplings of Azides and LUMO-Activated Unsaturated Acyl Azoliums. ACS Catalysis 2017, 7 (3) , 2139-2144. https://doi.org/10.1021/acscatal.6b03674
    76. Satoru Hiroto, Yoshihiro Miyake, and Hiroshi Shinokubo . Synthesis and Functionalization of Porphyrins through Organometallic Methodologies. Chemical Reviews 2017, 117 (4) , 2910-3043. https://doi.org/10.1021/acs.chemrev.6b00427
    77. Sampad Jana, Joice Thomas, and Wim Dehaen . A One-Pot Procedure for the Synthesis of “Click-Ready” Triazoles from Ketones. The Journal of Organic Chemistry 2016, 81 (24) , 12426-12432. https://doi.org/10.1021/acs.joc.6b02607
    78. Johan R. Johansson, Tamás Beke-Somfai, Anna Said Stålsmeden, and Nina Kann . Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications. Chemical Reviews 2016, 116 (23) , 14726-14768. https://doi.org/10.1021/acs.chemrev.6b00466
    79. Kapil Kumar, Debabrata Konar, Sandeep Goyal, Mukesh Gangar, Mangilal Chouhan, Ravindra K. Rawal, and Vipin A. Nair . Water-Promoted Regiospecific Azidolysis and Copper-Catalyzed Azide–Alkyne Cycloaddition: One-Pot Synthesis of 3-Hydroxy-1-alkyl-3-[(4-aryl/alkyl-1H-1,2,3-triazol-1-yl)methyl]indolin-2-ones. The Journal of Organic Chemistry 2016, 81 (20) , 9757-9764. https://doi.org/10.1021/acs.joc.6b01819
    80. Idrees Mohammed, Indrasena Reddy Kummetha, Gatikrushna Singh, Natalia Sharova, Gianluigi Lichinchi, Jason Dang, Mario Stevenson, and Tariq M. Rana . 1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New Class of Potent HIV-1 Vif Antagonists. Journal of Medicinal Chemistry 2016, 59 (16) , 7677-7682. https://doi.org/10.1021/acs.jmedchem.6b00247
    81. Kosuke Yamamoto, Theodora Bruun, Jung Yun Kim, Lei Zhang, and Mark Lautens . A New Multicomponent Multicatalyst Reaction (MC)2R: Chemoselective Cycloaddition and Latent Catalyst Activation for the Synthesis of Fully Substituted 1,2,3-Triazoles. Organic Letters 2016, 18 (11) , 2644-2647. https://doi.org/10.1021/acs.orglett.6b00975
    82. Zaira Monasterio, Aitziber Irastorza, José I. Miranda, and Jesus M. Aizpurua . Site-Selective N-Dealkylation of 1,2,3-Triazolium Salts: A Metal-Free Route to 1,5-Substituted 1,2,3-Triazoles and Related Bistriazoles. Organic Letters 2016, 18 (10) , 2511-2514. https://doi.org/10.1021/acs.orglett.6b01177
    83. Li-Li Zhu, Xiao-Qi Xu, Jin-Wei Shi, Bai-Ling Chen, and Zili Chen . N2-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N2-Alkyl-Substituted 1,2,3-Triazoles. The Journal of Organic Chemistry 2016, 81 (9) , 3568-3575. https://doi.org/10.1021/acs.joc.6b00185
    84. Vinod K. Tiwari, Bhuwan B. Mishra, Kunj B. Mishra, Nidhi Mishra, Anoop S. Singh, and Xi Chen . Cu-Catalyzed Click Reaction in Carbohydrate Chemistry. Chemical Reviews 2016, 116 (5) , 3086-3240. https://doi.org/10.1021/acs.chemrev.5b00408
    85. Shakir Ahamad, Ruchir Kant, and Kishor Mohanan . Metal-Free Three-Component Domino Approach to Phosphonylated Triazolines and Triazoles. Organic Letters 2016, 18 (2) , 280-283. https://doi.org/10.1021/acs.orglett.5b03437
    86. Maiara T. Saraiva, Gabriel P. Costa, Natália Seus, Ricardo F. Schumacher, Gelson Perin, Márcio W. Paixão, Rafael Luque, and Diego Alves . Room-Temperature Organocatalytic Cycloaddition of Azides with β-Keto Sulfones: Toward Sulfonyl-1,2,3-triazoles. Organic Letters 2015, 17 (24) , 6206-6209. https://doi.org/10.1021/acs.orglett.5b03196
    87. Steven B. Coffey, Gary Aspnes, and Allyn T. Londregan . Expedient Synthesis of N1-Substituted Triazole Peptidomimetics. ACS Combinatorial Science 2015, 17 (12) , 706-709. https://doi.org/10.1021/acscombsci.5b00150
    88. Xiaotian Qi, Heng Zhang, Ailong Shao, Lei Zhu, Ting Xu, Meng Gao, Chao Liu, and Yu Lan . Silver Migration Facilitates Isocyanide-Alkyne [3 + 2] Cycloaddition Reactions: Combined Experimental and Theoretical Study. ACS Catalysis 2015, 5 (11) , 6640-6647. https://doi.org/10.1021/acscatal.5b02009
    89. Jie-Ping Wan, Shuo Cao, and Yunyun Liu . A Metal- and Azide-Free Multicomponent Assembly toward Regioselective Construction of 1,5-Disubstituted 1,2,3-Triazoles. The Journal of Organic Chemistry 2015, 80 (18) , 9028-9033. https://doi.org/10.1021/acs.joc.5b01121
    90. Mei-Hua Shen, Ke Xu, Chu-Han Sun, and Hua-Dong Xu . The Reaction of 2,3-Dimethylimidazole-1-sulfonyl Azide Triflate with 3-Substituted Indoles: Reactivity and Scope. Organic Letters 2015, 17 (15) , 3654-3657. https://doi.org/10.1021/acs.orglett.5b01464
    91. Satoshi Okusu, Etsuko Tokunaga, and Norio Shibata . Difluoromethylation of Terminal Alkynes by Fluoroform. Organic Letters 2015, 17 (15) , 3802-3805. https://doi.org/10.1021/acs.orglett.5b01778
    92. Ting Li, Chen Fu, Zi Liu, Shuiliang Guo, Zicheng Liu, and Ting-Bin Wen . Half-Sandwich B-Oxy Boratabenzene Ruthenium Complexes: Synthesis, Characterization, and Reactivity of (η6-C5H5BOR)RuCl(PPh3)2 (R = Et, Me). Organometallics 2015, 34 (13) , 3292-3302. https://doi.org/10.1021/acs.organomet.5b00319
    93. Hui-Wen Bai, Zhong-Jian Cai, Shun-Yi Wang, and Shun-Jun Ji . Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions. Organic Letters 2015, 17 (12) , 2898-2901. https://doi.org/10.1021/acs.orglett.5b01000
    94. Fang Wei, Haoyu Li, Chuanling Song, Yudao Ma, Ling Zhou, Chen-Ho Tung, and Zhenghu Xu . Cu/Pd-Catalyzed, Three-Component Click Reaction of Azide, Alkyne, and Aryl Halide: One-Pot Strategy toward Trisubstituted Triazoles. Organic Letters 2015, 17 (11) , 2860-2863. https://doi.org/10.1021/acs.orglett.5b01342
    95. Sanjeev Kumar V. Vernekar, Li Qiu, Jing Zhang, Jayakanth Kankanala, Hongmin Li, Robert J. Geraghty, and Zhengqiang Wang . 5′-Silylated 3′-1,2,3-triazolyl Thymidine Analogues as Inhibitors of West Nile Virus and Dengue Virus. Journal of Medicinal Chemistry 2015, 58 (9) , 4016-4028. https://doi.org/10.1021/acs.jmedchem.5b00327
    96. K. Durga Bhaskar Yamajala, Mahendra Patil, and Shaibal Banerjee . Pd-Catalyzed Regioselective Arylation on the C-5 Position of N-Aryl 1,2,3-Triazoles. The Journal of Organic Chemistry 2015, 80 (6) , 3003-3011. https://doi.org/10.1021/jo5026145
    97. Huihui Chai, Ruiqiang Guo, Wei Yin, Lingping Cheng, Renhua Liu, and Changhu Chu . One-Pot, Three-Component Reaction Using Modified Julia Reagents: A Facile Synthesis of 4,5-Disubstituted 1,2,3-(NH)-Triazoles in a Wet Organic Solvent. ACS Combinatorial Science 2015, 17 (3) , 147-151. https://doi.org/10.1021/co5001597
    98. Yijin Su, Jeffrey L. Petersen, Tesia L. Gregg, and Xiaodong Shi . Ambient Benzotriazole Ring Opening through Intermolecular Radical Addition to Vinyltriazole. Organic Letters 2015, 17 (5) , 1208-1211. https://doi.org/10.1021/acs.orglett.5b00156
    99. Yunfeng Chen, Gang Nie, Qi Zhang, Shan Ma, Huan Li, and Qinquan Hu . Copper-Catalyzed [3 + 2] Cycloaddition/Oxidation Reactions between Nitro-olefins and Organic Azides: Highly Regioselective Synthesis of NO2-Substituted 1,2,3-Triazoles. Organic Letters 2015, 17 (5) , 1118-1121. https://doi.org/10.1021/ol503687w
    100. Jing-Mei Wang, Shang-Bo Yu, Zhi-Ming Li, Quan-Rui Wang, and Zhan-Ting Li . Mechanism of Samarium-Catalyzed 1,5-Regioselective Azide–Alkyne [3 + 2]-Cycloaddition: A Quantum Mechanical Investigation. The Journal of Physical Chemistry A 2015, 119 (8) , 1359-1368. https://doi.org/10.1021/jp5104615
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