Silver-Catalyzed Hydrotrifluoromethylation of Unactivated Alkenes with CF3SiMe3†
Xinyue Wu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
Search for more papers by this authorDr. Lingling Chu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Feng-Ling Qing
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620 (China)
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)===Search for more papers by this authorXinyue Wu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
Search for more papers by this authorDr. Lingling Chu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Feng-Ling Qing
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620 (China)
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 (China)===Search for more papers by this authorThis work was supported by the National Natural Science Foundation of China (21072028, 21272036) and the National Basic Research Program of China (2012CB21600).
Graphical Abstract
Zwischenzeitlich radikal: Die Titelreaktion führt zur selektiven Bildung trifluormethylierter Alkane und ist komplementär zur bekannten übergangsmetallkatalysierten Trifluormethylierung von Olefinen, die trifluormethylierte allylische Verbindungen ergibt. Mechanistische Studien deuten an, dass die Hydrotrifluormethylierung über ein CF3-Radikal verläuft.
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References
- 1
- 1aP. Kirsch, Modern Fluoroorganic Chemistry; Wiley-VCH, Weinheim, 2004;
10.1002/352760393X Google Scholar
- 1bK. Muller, C. Faeh, F. Diederich, Science 2007, 317, 1881;
- 1cM. Hird, Chem. Soc. Rev. 2007, 36, 2070;
- 1dK. L. Kirk, Org. Process Res. Dev. 2008, 12, 305.
- 2
- 2aM. Schlosser, Angew. Chem. 2006, 118, 5558;
10.1002/ange.200600449 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 5432;
- 2bJ.-A. Ma, D. Cahard, J. Fluorine Chem. 2007, 128, 975;
- 2cJ.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1;
- 2dA. Studer, Angew. Chem. 2012, 124, 9082; Angew. Chem. Int. Ed. 2012, 51, 8950.
- 3For recent reviews on transition-metal-mediated trifluoromethylation, see:
- 3aM. A. McClinton, D. A. McClinton, Tetrahedron 1992, 48, 6555;
- 3bS. Roy, B. T. Gregg, G. W. Gribble, V.-D. Le, S. Roy, Tetrahedron 2011, 67, 2161;
- 3cO. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475;
- 3dT. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470;
- 3eY. Ye, M. S. Sanford, Synlett 2012, 2005;
- 3fX.-F. Wu, H. Neumann, M. Beller, Chem. Asian J. 2012, 7, 1744;
- 3gT. Besset, C. Schneider, D. Cahard, Angew. Chem. 2012, 124, 5134;
10.1002/ange.201201012 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 5048;
- 3hF. Pan, Z. Shi, Acta Chim. Sin. 2012, 70, 1679;
- 3iF.-L. Qing, Chin. J. Org. Chem. 2012, 32, 815;
- 3jC. Lü, Q. Shen, D. Liu, Chin. J. Org. Chem. 2012, 32, 1380;
- 3kT. Liu, Q. Shen, Eur. J. Org. Chem. 2012, 6679.
- 4For palladium-mediated trifluoromethylation, see:
- 4aV. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2006, 128, 4632;
- 4bV. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2006, 128, 12644;
- 4cN. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2010, 132, 2878;
- 4dY. Ye, N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2010, 132, 14682;
- 4eN. D. Ball, J. B. Gary, Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 7577.
- 5For palladium-catalyzed trifluoromethylation, see:
- 5aX. Wang, L. Truesdale, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3648;
- 5bE. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson, S. L. Buchwald, Science 2010, 328, 1679;
- 5cX. Mu, S. Chen, X. Zhen, G. Liu, Chem. Eur. J. 2011, 17, 6039;
- 5dB. S. Samant, G. W. Kabalka, Chem. Commun. 2011, 47, 7236;
- 5eR. N. Loy, M. S. Sanford, Org. Lett. 2011, 13, 2548;
- 5fX. Mu, T. Wu, H.-y. Wang, Y.-l. Guo, G. Liu, J. Am. Chem. Soc. 2012, 134, 878;
- 5gX.-G. Zhang, H.-X. Dai, M. Wasa, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 11948.
- 6For copper-mediated trifluoromethylation, see:
- 6aG. G. Dubinina, H. Furutachi, D. A. Vicic, J. Am. Chem. Soc. 2008, 130, 8600;
- 6bL. Chu, F.-L. Qing, Org. Lett. 2010, 12, 5060;
- 6cT. D. Senecal, A. T. Parsons, S. L. Buchwald, J. Org. Chem. 2011, 76, 1174;
- 6dC.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, J.-C. Xiao, Angew. Chem. 2011, 123, 1936; Angew. Chem. Int. Ed. 2011, 50, 1896;
- 6eH. Morimoto, T. Tsubogo, N. D. Litvinas, J. F. Hartwig, Angew. Chem. 2011, 123, 3877;
10.1002/ange.201100633 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 3793;
- 6fO. A. Tomashenko, E. C. Escudero-Adan, M. M. Belmonte, V. V. Grushin, Angew. Chem. 2011, 123, 7797;
10.1002/ange.201101577 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 7655;
- 6gA. Zanardi, M. A. Novikov, E. Martin, J. Benet-Buchholz, V. V. Grushin, J. Am. Chem. Soc. 2011, 133, 20901;
- 6hN. D. Litvinas, P. S. Fier, J. F. Hartwig, Angew. Chem. 2012, 124, 551;
10.1002/ange.201106668 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 536;
- 6iB. A. Khan, A. E. Buba, L. J. Gooßen, Chem. Eur. J. 2012, 18, 1577;
- 6jP. Novák, A. Lishchynskyi, V. V. Grushin, Angew. Chem. 2012, 124, 7887; Angew. Chem. Int. Ed. 2012, 51, 7767;
- 6kY. Ye, S. Kunzi, M. S. Sanford, Org. Lett. 2012, 14, 4979;
- 6lM. Hu, C. Ni, J. Hu, J. Am. Chem. Soc. 2012, 134, 15257.
- 7For copepr-catalyzed trifluoromethylation, see:
- 7aM. Oishi, H. Kondo, H. Amii, Chem. Commun. 2009, 1909;
- 7bT. Knauber, F. Arikan, G.-V. Röschenthaler, L. J. Gooßen, Chem. Eur. J. 2011, 17, 2689;
- 7cZ. Weng, R. Lee, W. Jia, Y. Yuan, W. Wang, X. Feng, K.-W. Huang, Organometallics 2011, 30, 3229;
- 7dJ. Xu, D.-F. Luo, B. Xiao, Z.-J. Liu, T.-J. Gong, Y. Fu, L. Liu, Chem. Commun. 2011, 47, 4300;
- 7eT. Liu, Q. Shen, Org. Lett. 2011, 13, 2342;
- 7fT. Liu, X. Shao, Y. Wu, Q. Shen, Angew. Chem. 2012, 124, 555; Angew. Chem. Int. Ed. 2012, 51, 540;
- 7gL. Chu, F.-L. Qing, J. Am. Chem. Soc. 2012, 134, 1298;
- 7hX. L. Jiang, L. Chu, F.-L. Qing, J. Org. Chem. 2012, 77, 1251;
- 7iY. Huang, X. Fang, X. Lin, H. Li, W. He, K. W. Huang, Y. Yuan, Z. Weng, Tetrahedron 2012, 68, 9949;
- 7jY. Miyake, S. Ota, Y. Nishibayashi, Chem. Eur. J. 2012, 18, 13255;
- 7kY. Ye, M. S. Sanford, J. Am. Chem. Soc. 2012, 134, 9034;
- 7lD. Luo, J. Xu, Y. Fu, Q. X. Guo, Tetrahedron Lett. 2012, 53, 2769.
- 8
- 8aY. Ye, S. H. Lee, M. S. Sanford, Org. Lett. 2011, 13, 5464;
- 8bA. Hafner, S. Bräse, Angew. Chem. 2012, 124, 3773;
10.1002/ange.201107414 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 3713.
- 9
- 9aM. Naodovic, H. Yamamoto, Chem. Rev. 2008, 108, 3132;
- 9bJ.-M. Weibel, A. L. Blanc, P. Pale, Chem. Rev. 2008, 108, 3149.
- 10
- 10aT. Furuya, A. E. Strom, T. Ritter, J. Am. Chem. Soc. 2009, 131, 1662;
- 10bT. Furuya, T. Ritter, Org. Lett. 2009, 11, 2860;
- 10cP. Tang, T. Furuya, T. Ritter, J. Am. Chem. Soc. 2010, 132, 12150;
- 10dT. Furuya, J. E. M. N. Klein, T. Ritter, Synthesis 2010, 1804;
- 10eP. Tang, T. Ritter, Tetrahedron 2011, 67, 4449;
- 10fF. Yin, Z. Wang, Z. Li, C. Li, J. Am. Chem. Soc. 2012, 134, 10401;
- 10gT. Xu, G. Liu, Synlett 2012, 955.
- 11G. Teverovskiy, D. S. Surry, S. L. Buchwald, Angew. Chem. 2011, 123, 7450;
10.1002/ange.201102543 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 7312.
- 12C. Huang, T. Liang, S. Harada, E. Lee, T. Ritter, J. Am. Chem. Soc. 2011, 133, 13308.
- 13
- 13aA. T. Parsons, S. L. Buchwald, Angew. Chem. 2011, 123, 9286; Angew. Chem. Int. Ed. 2011, 50, 9120;
- 13bX. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 16410;
- 13cJ. Xu, Y. Fu, D. F. Luo, Y. Y. Jiang, B. Xiao, Z. J. Liu, T. J. Gong, L. Liu, J. Am. Chem. Soc. 2011, 133, 15300;
- 13dR. Shimizu, H. Egami, Y. Hamashima, M. Sodeoka, Angew. Chem. 2012, 124, 4655; Angew. Chem. Int. Ed. 2012, 51, 4577;
- 13eS. Mizuta, O. Galicia-López, K. M. Engle, S. Verhoog, K. Wheelhouse, G. Rassias, V. Gouverneur, Chem. Eur. J. 2012, 18, 8583.
- 14
- 14aP. G. Janson, I. Ghoneim, N. O. Ilchenko, K. J. Szabó, Org. Lett. 2012, 14, 2882;
- 14bY. Li, A. Studer, Angew. Chem. 2012, 124, 8345; Angew. Chem. Int. Ed. 2012, 51, 8221;
- 14cY. Yasu, T. Koike, M. Akita, Angew. Chem. 2012, 124, 9705;
10.1002/ange.201205071 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 9567;
- 14dH. Egami, R. Shimizu, M. Sodeoka, Tetrahedron Lett. 2012, 53, 5503;
- 14eR. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2012, 134, 12462;
- 14fC. Feng, T.-P. Loh, Chem. Sci. 2012, 3, 3458.
- 15L. Chu, F.-L. Qing, Org. Lett. 2012, 14, 2106.
- 16Electrochemical hydrotrifluoromethylation, see:
- 16aN. Muller, J. Org. Chem. 1986, 51, 263;
- 16bN. Muller, J. Fluorine Chem. 1987, 36, 163;
- 16cK. Uneyama, S. Watanbe, J. Org. Chem. 1990, 55, 3909;
- 16dK. Uneyama, S. Watanabe, Y. Tokunaga, K. Kitagawa, Y. Sato, Bull. Chem. Soc. Jpn. 1992, 65, 1976;
- 16eY. Dan-oh, K. Uneyama, Bull. Chem. Soc. Jpn. 1995, 68, 2993;
- 16fJ.-B. Tommasino, A. Brondex, M. Médebielle, M. Thomalla, B. R. Langlois, T. Billard, Synlett 2002, 1697;
- 16gP. Wang, Y. Tang, D. A. Tirrell, J. Am. Chem. Soc. 2003, 125, 6900.
- 17For hydrotrifluoromethylation of α,β-unsaturated ketones or acyl-oxazolidiones, see:
- 17aK. Sato, M. Omote, A. Ando, I. Kumadaki, Org. Lett. 2004, 6, 4359;
- 17bH. Erdbrink, I. Peuser, U. I. M. Gerling, D. Lentz, B. Koksch, C. Czekelius, Org. Biomol. Chem. 2012, 10, 8583.
- 18
- 18aK. Maruoka, H. Sano, Y. Fukutani, H. Yamamoto, Chem. Lett. 1985, 1689;
- 18bJ. Ignatowska, W. Dmowski, J. Fluorine Chem. 2007, 128, 997.
- 19
- 19aM. Hanack, H. Meyer, Justus Liebigs Ann. Chem. 1968, 720, 81;
- 19bZ. Liu, K. Kumar, Synthesis 2010, 1905.
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