Nickel-Catalyzed Decarboxylative Difluoroalkylation of α,β-Unsaturated Carboxylic Acids
Gang Li
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorTao Wang
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorFan Fei
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorDr. Yi-Ming Su
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorDr. Yan Li
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorDr. Quan Lan
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xi-Sheng Wang
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Shanghai, 200032 China
Search for more papers by this authorGang Li
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorTao Wang
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorFan Fei
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorDr. Yi-Ming Su
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorDr. Yan Li
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorDr. Quan Lan
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xi-Sheng Wang
Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Shanghai, 200032 China
Search for more papers by this authorAbstract
The first example of nickel-catalyzed decarboxylative fluoroalkylation of α,β-unsaturated carboxylic acids has been developed with commonly available fluoroalkyl halides. This novel transformation has demonstrated broad substrate scope, excellent functional-group tolerance, mild reaction conditions, and excellent stereoselectivity. Mechanistic investigations indicate that a fluoroalkyl radical is involved in the catalytic cycle.
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References
- 1K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881.
- 2
- 2aB. E. Smart, J. Fluorine Chem. 2001, 109, 3;
- 2bP. Kirsch, Modern Fluoroorganic Chemistry: Synthesis Reactivity, Applications, 2nd ed., Wiley-VCH, Weinheim, 2013;
10.1002/9783527651351 Google Scholar
- 2cP. Jeschke, ChemBioChem 2004, 5, 570;
- 2dS. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320.
- 3
- 3aR. F. Wallin, B. M. Regan, M. D. Napoli, I. J. Stern, Anesth. Analg. 1975, 54, 758;
- 3bG. S. Prakash, S. Chacko, Curr. Opin. Drug Discovery Dev. 2008, 11, 793;
- 3cJ. Hu, W. Zhang, F. Wang, Chem. Commun. 2009, 7465;
- 3dD. Y. Mikhaylov, Y. H. Budnikova, Russ. Chem. Rev. 2013, 82, 835;
- 3eS. Barata-Vallejo, B. Lantaño, A. Postigo, Chem. Eur. J. 2014, 20, 16806;
- 3fC. Ni, L. Zhu, J. Hu, Acta Chim. Sin. 2015, 73, 90;
- 3gM.-C. Belhomme, T. Besset, T. Poisson, X. Pannecoucke, Chem. Eur. J. 2015, 21, 12836.
- 4For selected reviews on fluoroalkylation, see:
- 4aB. R. Langlois, T. Billard, S. Roussel, J. Fluorine Chem. 2005, 126, 173;
- 4bM. Schlosser, Angew. Chem. Int. Ed. 2006, 45, 5432; Angew. Chem. 2006, 118, 5558;
- 4cJ.-A. Ma, D. Cahard, J. Fluorine Chem. 2007, 128, 975;
- 4dT. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470;
- 4eO. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475;
- 4fZ. Jin, G. B. Hammond, B. Xu, Aldrichimica Acta 2012, 45, 67;
- 4gC.-P. Zhang, Q.-Y. Chen, Y. Guo, J.-C. Xiao, Y.-C. Gu, Chem. Soc. Rev. 2012, 41, 4536;
- 4hC. Hollingworth, V. Gouverneur, Chem. Commun. 2012, 48, 2929;
- 4iT. Besset, C. Schneider, D. Cahard, Angew. Chem. Int. Ed. 2012, 51, 5048; Angew. Chem. 2012, 124, 5134;
- 4jW. Zhang, C. Ni, J. Hu, Top. Curr. Chem. 2012, 308, 25;
- 4kX. Liu, C. Xu, M. Wang, Q. Liu, Chem. Rev. 2015, 115, 683;
- 4lC. Ni, M. Hu, J. Hu, Chem. Rev. 2015, 115, 765.
- 5
- 5aE. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson, S. L. Buchwald, Science 2010, 328, 1679;
- 5bC. Guo, R.-W. Wang, F.-L. Qing, J. Fluorine Chem. 2012, 143, 135;
- 5cZ. Feng, Q.-Q. Min, Y.-L. Xiao, B. Zhang, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 1669; Angew. Chem. 2014, 126, 1695;
- 5dY.-B. Yu, G.-Z. He, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 10457; Angew. Chem. 2014, 126, 10625;
- 5eQ.-Q. Min, Z. Yin, Z. Feng, W.-H. Guo, X. Zhang, J. Am. Chem. Soc. 2014, 136, 1230;
- 5fE. P. A. Talbot, T. A. Fernandes, J. M. McKenna, F. D. Toste, J. Am. Chem. Soc. 2014, 136, 4101;
- 5gY.-L. Xiao, B. Zhang, Z. Feng, X. Zhang, Org. Lett. 2014, 16, 4822;
- 5hC. Shao, G. Shi, Y. Zhang, S. Pan, X. Guan, Org. Lett. 2015, 17, 2652;
- 5iD. Chang, Y. Gu, Q. Shen, Chem. Eur. J. 2015, 21, 6074;
- 5jZ. Feng, Q.-Q. Min, H.-Y. Zhao, J.-W. Gu, X. Zhang, Angew. Chem. Int. Ed. 2015, 54, 1270; Angew. Chem. 2015, 127, 1286;
- 5kJ.-W. Gu, W.-H. Guo, X. Zhang, Org. Chem. Front. 2015, 2, 38;
- 5lF. Zhang, Q.-Q. Min, X. Zhang, Synthesis 2015, 47, 2912;
- 5mJ. Hu, B. Gao, L. Li, C. Ni, J. Hu, Org. Lett. 2015, 17, 3086;
- 5nJ.-W. Gu, X. Zhang, Org. Lett. 2015, 17, 5384.
- 6
- 6aM. Oishi, H. Konodo, H. Amii, Chem. Commun. 2009, 1909;
- 6bZ. Feng, F. Chen, X. Zhang, Org. Lett. 2012, 14, 1938;
- 6cY. Zhao, B. Gao, C. Ni, J. Hu, Org. Lett. 2012, 14, 6080;
- 6dQ. Qi, Q. Shen, L. Lu, J. Am. Chem. Soc. 2012, 134, 6548;
- 6eM. Hu, C. Ni, J. Hu, J. Am. Chem. Soc. 2012, 134, 15257;
- 6fZ. He, M. Hu, T. Luo, L. Li, J. Hu, Angew. Chem. Int. Ed. 2012, 51, 11545; Angew. Chem. 2012, 124, 11713;
- 6gY. Ye, M. S. Sanford, J. Am. Chem. Soc. 2013, 135, 4648;
- 6hZ. Feng, Y.-L. Xiao, X. Zhang, Org. Chem. Front. 2014, 1, 113;
- 6iM.-C. Belhomme, T. Poisson, X. Pannecoucke, J. Org. Chem. 2014, 79, 7205;
- 6jJ. Saavedra-Olavarría, G. C. Arteaga, J. J. López, E. G. Pérez, Chem. Commun. 2015, 51, 3379;
- 6kX. Li, J. Zhao, L. Zhang, M. Hu, L. Wang, J. Hu, Org. Lett. 2015, 17, 298;
- 6lJ. Zhu, C. Ni, B. Gao, J. Hu, J. Fluorine Chem. 2015, 171, 139.
- 7
- 7aY. Liang, G. C. Fu, J. Am. Chem. Soc. 2014, 136, 5520;
- 7bX. Jiang, S. Sakthivel, K. Kulbitski, G. Nisnevich, M. Gandelman, J. Am. Chem. Soc. 2014, 136, 9548;
- 7cY.-L. Xiao, W.-H. Guo, G.-Z. He, Q. Pan, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 9909; Angew. Chem. 2014, 126, 10067;
- 7dY.-M. Su, G.-S. Feng, Z.-Y. Wang, Q. Lan, X.-S. Wang, Angew. Chem. Int. Ed. 2015, 54, 6003; Angew. Chem. 2015, 127, 6101;
- 7eX. Jiang, M. Gandelman, J. Am. Chem. Soc. 2015, 137, 2542;
- 7fL. An, Y.-L. Xiao, Q.-Q. Min, X. Zhang, Angew. Chem. Int. Ed. 2015, 54, 9079; Angew. Chem. 2015, 127, 9207;
- 7gY.-L. Xiao, Q. Qiang, X. Zhang, Acta Chim. Sin. 2015, 73, 387; for Ni0-catalyzed fluoroalkyaltion of vinylzirconiums, see:
- 7hM. K. Schwaebe, J. R. McCarthy, J. P. Whitten, Tetrahedron Lett. 2000, 41, 791; for nickel(0)-catalyzed free-radical perfluoroalkylations of electron-rich (hetero)arenes, see:
- 7iQ.-L. Zhou, Y.-Z. Huang, J. Fluorine Chem. 1989, 43, 385;
- 7jX.-T. Huang, Q.-Y. Chen, J. Org. Chem. 2001, 66, 4651.
- 8For recent reviews of decarboxylative cross-coupling reactions, see:
- 8aL. J. Gooßen, F. Collet, K. Gooßen, Isr. J. Chem. 2010, 50, 617;
- 8bN. Rodríguez, L. J. Goossen, Chem. Soc. Rev. 2011, 40, 5030;
- 8cR. Shang, L. Liu, Sci. China Chem. 2011, 54, 1670;
- 8dW. I. Dzik, P. P. Lange, L. J. Gooßen, Chem. Sci. 2012, 3, 2671;
- 8eJ. Cornella, I. Larrosa, Synthesis 2012, 44, 653.
- 9For either copper or iridium-catalyzed decarboxylative fluoroalkylations using electrophilic fluoroalkylation reagents, see:
- 9aZ. He, T. Luo, M. Hu, Y. Cao, J. Hu, Angew. Chem. Int. Ed. 2012, 51, 3944; Angew. Chem. 2012, 124, 4010;
- 9bP. Xu, A. Abdukader, K. Hu, Y. Cheng, C. Zhu, Chem. Commun. 2014, 50, 2308; for a copper- and iron-catalyzed example employing an excess amount of oxidant, see:
- 9cZ. Li, Z. Cui, Z.-Q. Liu, Org. Lett. 2013, 15, 406.
- 10
- 10aG. D. Jones, J. L. Martin, C. McFarland, O. R. Allen, R. E. Hall, A. D. Haley, R. J. Brandon, T. Konovalova, P. J. Desrochers, P. Pulay, D. A. Vicic, J. Am. Chem. Soc. 2006, 128, 13175;
- 10bV. B. Phapale, E. Buñuel, M. García-Iglesias, D. J. Cárdenas, Angew. Chem. Int. Ed. 2007, 46, 8790; Angew. Chem. 2007, 119, 8946;
- 10cX. Lin, D. L. Phillips, J. Org. Chem. 2008, 73, 3680;
- 10dX. Hu, Chem. Sci. 2011, 2, 1867;
- 10eZ. Lu, A. Wilsily, G. C. Fu, J. Am. Chem. Soc. 2011, 133, 8154;
- 10fA. Wilsily, F. Tramutola, N. A. Owston, G. C. Fu, J. Am. Chem. Soc. 2012, 134, 5794;
- 10gJ. Choi, G. C. Fu, J. Am. Chem. Soc. 2012, 134, 9102;
- 10hC. Liu, S. Tang, D. Liu, J. Yuan, L. Zheng, L. Meng, A. Lei, Angew. Chem. Int. Ed. 2012, 51, 3638; Angew. Chem. 2012, 124, 3698;
- 10iS. L. Zultanski, G. C. Fu, J. Am. Chem. Soc. 2013, 135, 624;
- 10jJ. Cornella, E. Gómez-Bengoa, R. Martin, J. Am. Chem. Soc. 2013, 135, 1997;
- 10kD. Liu, C. Liu, H. Li, A. Lei, Angew. Chem. Int. Ed. 2013, 52, 4453; Angew. Chem. 2013, 125, 4549;
- 10lA. Correa, T. León, R. Martin, J. Am. Chem. Soc. 2014, 136, 1062;
- 10mD. A. Everson, D. J. Weix, J. Org. Chem. 2014, 79, 4793;
- 10nG. Yin, I. Kalvet, U. Englert, F. Schoenebeck, J. Am. Chem. Soc. 2015, 137, 4164;
- 10oL. An, Y.-L. Xiao, Q.-Q. Min, X. Zhang, Angew. Chem. Int. Ed. 2015, 54, 9079; Angew. Chem. 2015, 127, 9207; see also Ref. [7d] and [7g].
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