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[해외논문] Transformation of tert‐Butyl Amide Directing Groups to Nitriles in Iridium‐Catalyzed C−H Bond Functionalizations

Asian journal of organic chemistry, v.10 no.12, 2021년, pp.3411 - 3420  

Kim, Dopil (Department of Chemistry Chungbuk National University Cheongju 28644 Republic of Korea) ,  Yoo, Haneul (Department of Chemistry Chungbuk National University Cheongju 28644 Republic of Korea) ,  Park, Myung Hwan (Department of Chemistry Education Chungbuk National University Cheongju 28644 Republic of Korea) ,  Kim, Youngjo (Department of Chemistry Chungbuk National University Cheongju 28644 Republic of Korea) ,  Chuang, Gary Jing (Department of Chemistry Chung Yuan Christian University Taoyuan 32023 Taiwan) ,  Yoo, Kwangho (Inorganic Chemistry I Ruhr-Universitat Bochum Bochum 44780 Germany) ,  Kim, Dongwook (Center for Catalytic Hydrocarbon Functionalization Institute for Basic Science Daejeon 34141 Republic of Korea) ,  Kim, Hyun Jin (Innovative Therapeutic Research Center Therapeutics and Biotechnology Division Korea Research Institute of Chemical Technology (KRICT) Daejeon 34114 Republic of Korea) ,  Kim, Min (Department of Chemistry Chungbuk National University Cheongju 28644 Republic of Korea)

Abstract AI-Helper 아이콘AI-Helper

AbstractTo overcome limitations of the directing group in IrCp* catalysis for C−H functionalization, we developed a directing group transformation strategy that was applied after obtaining the desired products. Well‐established Ir‐catalyzed alkenylation, alkylation, and arylatio...

참고문헌 (66)

  1. Kuhl, Nadine, Hopkinson, Matthew N., Wencel‐Delord, Joanna, Glorius, Frank. Beyond Directing Groups: Transition‐Metal‐Catalyzed CH Activation of Simple Arenes. Angewandte Chemie. international edition, vol.51, no.41, 10236-10254.

  2. Sambiagio, Carlo, Schönbauer, David, Blieck, Remi, Dao-Huy, Toan, Pototschnig, Gerit, Schaaf, Patricia, Wiesinger, Thomas, Zia, Muhammad Farooq, Wencel-Delord, Joanna, Besset, Tatiana, Maes, Bert U. W., Schnürch, Michael. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry. Chemical Society reviews, vol.47, no.17, 6603-6743.

  3. Rej, Supriya, Ano, Yusuke, Chatani, Naoto. Bidentate Directing Groups: An Efficient Tool in C-H Bond Functionalization Chemistry for the Expedient Construction of C-C Bonds. Chemical reviews, vol.120, no.3, 1788-1887.

  4. Xia, Ying, Dong, Guangbin. Temporary or removable directing groups enable activation of unstrained C-C bonds. Nature reviews. Chemistry, vol.4, no.11, 600-614.

  5. Gandeepan, Parthasarathy, Ackermann, Lutz. Transient Directing Groups for Transformative C-H Activation by Synergistic Metal Catalysis. Chem, vol.4, no.2, 199-222.

  6. St John-Campbell, Sahra, Bull, James A.. Transient imines as ‘next generation’ directing groups for the catalytic functionalisation of C-H bonds in a single operation. Organic & biomolecular chemistry, vol.16, no.25, 4582-4595.

  7. Goswami, Nupur, Bhattacharya, Trisha, Maiti, Debabrata. Transient directing ligands for selective metal-catalysed C-H activation. Nature reviews. Chemistry, vol.5, no.9, 646-659.

  8. Ha, Hyeonbin, Lee, Jooyeon, Park, Myung Hwan, Jung, Byunghyuck, Kim, Min. Transient Directing Group‐Assisted C─H Bond Functionalization of Aliphatic Amines: Strategies for Efficiency and Site‐Selectivity. Bulletin of the Korean chemical society, vol.41, no.6, 582-587.

  9. Font, Marc, Quibell, Jacob M., Perry, Gregory J. P., Larrosa, Igor. The use of carboxylic acids as traceless directing groups for regioselective C-H bond functionalisation. Chemical communications : Chem comm, vol.53, no.41, 5584-5597.

  10. Wei, Ye, Hu, Peng, Zhang, Min, Su, Weiping. Metal-Catalyzed Decarboxylative C–H Functionalization. Chemical reviews, vol.117, no.13, 8864-8907.

  11. Huang, Chunhui, Chernyak, Natalia, Dudnik, Alexander S., Gevorgyan, Vladimir. The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho‐Acyloxylation and ortho‐Halogenation Reactions of Arenes. Advanced synthesis & catalysis, vol.353, no.8, 1285-1305.

  12. Parasram, Marvin, Gevorgyan, Vladimir. Silicon-Tethered Strategies for C–H Functionalization Reactions. Accounts of chemical research, vol.50, no.8, 2038-2053.

  13. Neufeldt, Sharon R., Sanford, Melanie S.. O-Acetyl Oximes as Transformable Directing Groups for Pd-Catalyzed C−H Bond Functionalization. Organic letters, vol.12, no.3, 532-535.

  14. Zhang, Wei, Wei, Jun, Fu, Shaomin, Lin, Dongen, Jiang, Huanfeng, Zeng, Wei. Highly Stereoselective Ruthenium(II)-Catalyzed Direct C2-syn-Alkenylation of Indoles with Alkynes. Organic letters, vol.17, no.6, 1349-1352.

  15. Tang, Jiaxu, Tang, Yuhai, Wang, Xiaonan, Wang, Yongzhuang, Huang, Xiaoli, Xu, Silong, Li, Yang. Regioselective cascade annulation of indoles with alkynediones for construction of functionalized tetrahydrocarbazoles triggered by Cp*RhIII-catalyzed C-H activation. Organic chemistry frontiers : an international journal of organic chemistry, vol.8, no.14, 3809-3814.

  16. Li, Xianwei, Ouyang, Wensen, Nie, Jianhong, Ji, Shaomin, Chen, Qian, Huo, Yanping. Recent Development on Cp*Ir(III)‐Catalyzed C−H Bond Functionalization. ChemCatChem, vol.12, no.9, 2358-2384.

  17. Park, Juhyeon, Chang, Sukbok. Comparison of the Reactivities and Selectivities of Group 9 [Cp*MIII] Catalysts in C−H Functionalization Reactions. Chemistry, an Asian journal, vol.13, no.9, 1089-1102.

  18. Shipilovskikh, Sergei A., Vaganov, Vladimir Yu., Denisova, Elena I., Rubtsov, Aleksandr E., Malkov, Andrei V.. Dehydration of Amides to Nitriles under Conditions of a Catalytic Appel Reaction. Organic letters, vol.20, no.3, 728-731.

  19. Kuo, Chun-Wei, Zhu, Jia-Liang, Wu, Jen-Dar, Chu, Cheng-Ming, Yao, Ching-Fa, Shia, Kak-Shan. A convenient new procedure for converting primary amides into nitriles. Chemical communications : Chem comm, vol.2007, no.3, 301-303.

  20. Yadav, L.D.S., Srivastava, V.P., Patel, R.. Bromodimethylsulfonium bromide (BDMS): a useful reagent for conversion of aldoximes and primary amides to nitriles. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.50, no.39, 5532-5535.

  21. Talbi, Imen, Efrit, Mohamed Lotfi, Touil, Soufiane. Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe2)3, PCl3, or P(OPh)3. ACS omega, vol.3, no.5, 5078-5082.

  22. 10.1021/jo020005 

  23. Elangovan, Saravanakumar, Quintero-Duque, Samuel, Dorcet, Vincent, Roisnel, Thierry, Norel, Lucie, Darcel, Christophe, Sortais, Jean-Baptiste. Knölker-Type Iron Complexes Bearing an N-Heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides. Organometallics, vol.34, no.18, 4521-4528.

  24. Zhou, Shaolin, Addis, Daniele, Das, Shoubhik, Junge, Kathrin, Beller, Matthias. New catalytic properties of iron complexes: dehydration of amides to nitriles. Chemical communications : Chem comm, vol.2009, no.32, 4883-4885.

  25. Xue, B., Sun, H., Wang, Y., Zheng, T., Li, X., Fuhr, O., Fenske, D.. Efficient reductive dehydration of primary amides to nitriles catalyzed by hydrido thiophenolato iron(II) complexes under hydrosilation conditions. Catalysis communications, vol.86, 148-150.

  26. Al-Huniti, Mohammed H., Rivera-Chávez, José, Colón, Katsuya L., Stanley, Jarrod L., Burdette, Joanna E., Pearce, Cedric J., Oberlies, Nicholas H., Croatt, Mitchell P.. Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides To Form Nitriles. Organic letters, vol.20, no.19, 6046-6050.

  27. Maffioli, S. I., Marzorati, E., Marazzi, A.. Mild and Reversible Dehydration of Primary Amides with PdCl2 in Aqueous Acetonitrile. Organic letters, vol.7, no.23, 5237-5239.

  28. Enthaler, Stephan, Inoue, Shigeyoshi. An Efficient Zinc‐Catalyzed Dehydration of Primary Amides to Nitriles. Chemistry, an Asian journal, vol.7, no.1, 169-175.

  29. Manjula, Krishnappa, Pasha, Mohamed Afzal. Rapid Method of Converting Primary Amides to Nitriles and Nitriles to Primary Amides by ZnCl2 using Microwaves under Different Reaction Conditions. Synthetic communications, vol.37, no.9, 1545-1550.

  30. Perni, Robert B., Gribble, Gordon W.. THE VON BRAUN REACTION BETWEEN N-t-BUTYLAMIDES AND PHOSPHORUS OXYCHLORIDE. A CONVENIENT NITRILE SYNTHESIS. Organic preparations and procedures international, vol.15, no.5, 297-302.

  31. Geng, H., Huang, P.Q.. Versatile and chemoselective transformation of aliphatic and aromatic secondary amides to nitriles. Tetrahedron, vol.71, no.23, 3795-3801.

  32. Vaughan, Wyman R., Carlson, Richard D.. The von Braun Reaction. I. Scope and Limitations. Journal of the American Chemical Society, vol.84, no.5, 769-774.

  33. Phillips, B.A., Fodor, G., Gal, J., Letourneau, F., Ryan, J.J.. Mechanism of the von Braun amide degradations with carbonyl bromide or phosphorus pentabromide. Tetrahedron, vol.29, no.21, 3309-3327.

  34. Shabashov, Dmitry, Maldonado, Jesús R. Molina, Daugulis, Olafs. Carbon−Hydrogen Bond Functionalization Approach for the Synthesis of Fluorenones and ortho-Arylated Benzonitriles. Journal of organic chemistry, vol.73, no.19, 7818-7821.

  35. Bargar, T. M., Riley, C. M.. A Rapid and Efficient Method for Dehydration of Primary Amides to Nitriles. Preparation of Acrylonitrile Derivatives. Synthetic communications, vol.10, no.6, 479-487.

  36. Kim, Jiyu, Park, Sung-Woo, Baik, Mu-Hyun, Chang, Sukbok. Complete Switch of Selectivity in the C–H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups. Journal of the American Chemical Society, vol.137, no.42, 13448-13451.

  37. Ping, Yuanyuan, Wang, Liping, Ding, Qiuping, Peng, Yiyuan. Nitrile as a Versatile Directing Group for C(sp2)-H Functionalizations. Advanced synthesis & catalysis, vol.359, no.19, 3274-3291.

  38. Wan, Jung-Chih, Huang, Jun-Min, Jhan, Yu-Huei, Hsieh, Jen-Chieh. Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation. Organic letters, vol.15, no.11, 2742-2745.

  39. Kakiuchi, Fumitoshi, Sonoda, Motohiro, Tsujimoto, Takuya, Chatani, Naoto, Murai, Shinji. The Ruthenium-Catalyzed Addition of C-H Bonds in Aromatic Nitriles to Olefins. Chemistry letters, vol.28, no.10, 1083-1084.

  40. Li, Wu, Xu, Zhipeng, Sun, Peipei, Jiang, Xiaoqing, Fang, Min. Synthesis of Biphenyl-2-carbonitrile Derivatives via a Palladium-Catalyzed sp2 C−H Bond Activation Using Cyano as a Directing Group. Organic letters, vol.13, no.6, 1286-1289.

  41. Reddy, Mallu Chenna, Jeganmohan, Masilamani. Ruthenium-Catalyzed Cyclization of Aromatic Nitriles with Alkenes: Stereoselective Synthesis of (Z)-3-Methyleneisoindolin-1-ones. Organic letters, vol.16, no.18, 4866-4869.

  42. Kumar, Ravi, Arigela, Rajesh K., Kundu, Bijoy. Unprecedented Transformation of a Directing Group Generated In Situ and Its Application in the One‐Pot Synthesis of 2‐Alkenyl Benzonitriles. Chemistry : a European journal, vol.21, no.33, 11807-11812.

  43. Manikandan, Rajendran, Madasamy, Padmaja, Jeganmohan, Masilamani. Ruthenium-Catalyzed ortho Alkenylation of Aromatics with Alkenes at Room Temperature with Hydrogen Evolution. ACS catalysis, vol.6, no.1, 230-234.

  44. Reddy, Mallu Chenna, Jeganmohan, Masilamani. Ruthenium-catalyzed ortho alkenylation of aromatic nitriles with activated alkenes via C–H bond activation. Chemical communications : Chem comm, vol.51, no.53, 10738-10741.

  45. Reddy, R. Santhosh, Kiran, I. N. Chaithanya, Sudalai, Arumugam. CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: a facile entry to 3-substituted chiral phthalides. Organic & biomolecular chemistry, vol.10, no.18, 3655-3661.

  46. Manikandan, Rajendran, Jeganmohan, Masilamani. Ruthenium-Catalyzed Cyclization of Anilides with Substituted Propiolates or Acrylates: An Efficient Route to 2-Quinolinones. Organic letters, vol.16, no.13, 3568-3571.

  47. Han, Wen‐Jing, Pu, Fan, Fan, Juan, Liu, Zhong‐Wen, Shi, Xian‐Ying. Rhodium(III)‐Catalyzed Tandem C−H Olefination and Oxidative Cyclization of Aromatic Acids with Acrylates for the Synthesis of (E)‐3‐Ylidenephthalides. Advanced synthesis & catalysis, vol.359, no.20, 3520-3525.

  48. Chen, Lili, Li, Hongji, Yu, Feng, Wang, Lei. Ru-catalyzed decarboxylative cyclization of mandelic acids with acrylates: facile access to the phthalide skeleton. Chemical communications : Chem comm, vol.50, no.94, 14866-14869.

  49. Xia, Ying, Liu, Zhen, Feng, Sheng, Zhang, Yan, Wang, Jianbo. Ir(III)-Catalyzed Aromatic C-H Bond Functionalization via Metal Carbene Migratory Insertion. Journal of organic chemistry, vol.80, no.1, 223-236.

  50. Shin, Kwangmin, Park, Sung-Woo, Chang, Sukbok. Cp*Ir(III)-Catalyzed Mild and Broad C−H Arylation of Arenes and Alkenes with Aryldiazonium Salts Leading to the External Oxidant-Free Approach. Journal of the American Chemical Society, vol.137, no.26, 8584-8592.

  51. Miura, T., Harumashi, T., Murakami, M.. Cyclization Reaction of Cyano-Substituted Unsaturated Esters Prompted by Conjugate Addition of Organoborons. Organic letters, vol.9, no.5, 741-743.

  52. Beugelmans, R., Bois-Choussy, M., Boudet, B.. Studies on SRN1 reactions. Part 8 - New and direct arylation and hetarylation of β-dicarbonyl compounds by SRN1. Tetrahedron, vol.38, no.23, 3479-3483.

  53. Mei, Tian-Sheng, Wang, Dong-Hui, Yu, Jin-Quan. Expedient Drug Synthesis and Diversification via ortho-C−H Iodination using Recyclable PdI2 as the Precatalyst. Organic letters, vol.12, no.14, 3140-3143.

  54. Jiang, Bo, Wu, Songxiao, Zeng, Jing, Yang, Xiaobo. Controllable Rh(III)-Catalyzed C-H Arylation and Dealcoholization: Access to Biphenyl-2-carbonitriles and Biphenyl-2-carbimidates. Organic letters, vol.20, no.20, 6573-6577.

  55. Huang, Liangbin, Ackerman, Laura K. G., Kang, Kai, Parsons, Astrid M., Weix, Daniel J.. LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates. Journal of the American Chemical Society, vol.141, no.28, 10978-10983.

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