Palladium-Catalyzed Catellani ortho-Acylation Reaction: An Efficient and Regiospecific Synthesis of Diaryl Ketones
Yunze Huang
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)
Search for more papers by this authorRui Zhu
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)
Search for more papers by this authorKun Zhao
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenhua Gu
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)Search for more papers by this authorYunze Huang
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)
Search for more papers by this authorRui Zhu
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)
Search for more papers by this authorKun Zhao
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhenhua Gu
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026 (P.R. China)Search for more papers by this authorAbstract
A palladium-catalyzed, norbornene-mediated Catellani ortho-acylation reaction was developed by the use of either acyl chlorides or acid anhydrides as acylation reagents. The addition of more than a stoichiometric amount of H2O is crucial for this transformation when acid chlorides are used, and kinetic studies indicate that the active acylation reagent is possibly an acid anhydride.
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References
- 1
- 1aR. K. Dieter, Tetrahedron 1999, 55, 4177;
- 1bN. J. Lawrence, J. Chem. Soc. Perkin Trans. 1 1998, 1739;
- 1cQ.-F. Hu, B. Zhou, J.-M. Huang, X.-M. Gao, L.-D. Shu, G.-Y. Yang, C.-T. Che, J. Nat. Prod. 2013, 76, 292;
- 1dA. Shimada, I. Takahashi, T. Kawano, Y. Kimura, Z. Naturforsch. B 2011, 56, 797.
- 2M. B. Hadimani, M. T. MacDonough, A. Ghatak, T. E. Strecker, R. Lopez, M. Sriram, B. L. Nguyen, J. J. Hall, R. J. Kessler, A. R. Shirali, L. Liu, C. M. Garner, G. R. Pettit, E. Hamel, D. J. Chaplin, R. P. Mason, M. L. Trawick, K. G. Pinney, J. Nat. Prod. 2013, 76, 1668.
- 3S.-M. Zhao, Z. Wang, G.-Z. Zeng, W.-W. Song, X.-Q. Chen, X.-N. Li, N.-H. Tan, Org. Lett. 2014, 16, 5576.
- 4H. Kim, I. Yang, S.-Y. Ryu, D. H. Won, A. G. Giri, W. Wang, H. Choi, J. Chin, D. Hahn, E. Kim, C. Han, J. Lee, S.-J. Nam, W.-K. Ho, H. Kang, J. Nat. Prod. 2015, 78, 363.
- 5C. Duplais, F. Bures, I. Sapountzis, T. J. Korn, G. Cahiez, P. Knochel, Angew. Chem. Int. Ed. 2004, 43, 2968; Angew. Chem. 2004, 116, 3028.
- 6For a most recent review, see:
- 6aX.-F. Wu, Chem. Eur. J. 2015, 21, 12252; for some typical transition-metal-catalyzed acylation reactions, see:
- 6bX. Jia, S. Zhang, W. Wang, F. Luo, J. Cheng, Org. Lett. 2009, 11, 3120;
- 6cQ. Shuai, L. Yang, X. Guo, O. Basle, C.-J. Li, J. Am. Chem. Soc. 2010, 132, 12212;
- 6dR. Giri, J. K. Lam, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 686;
- 6eY. Lu, D. Leow, X. Wang, K. M. Engle, J.-Q. Yu, Chem. Sci. 2011, 2, 967;
- 6fS. D. Ramgren, N. K. Garg, Org. Lett. 2014, 16, 824;
- 6gZ. Yin, P. Sun, J. Org. Chem. 2012, 77, 11339;
- 6hQ. Zhang, F. Yang, Y. Wu, Chem. Commun. 2013, 49, 6837;
- 6iC. Pi, X. Cui, X. Liu, M. Guo, H. Zhang, Y. Wu, Org. Lett. 2014, 16, 5164;
- 6jC. W. Chan, Z. Zhou, A. S. C. Chan, W. Y. Yu, Org. Lett. 2010, 12, 3926;
- 6kP. Mamone, G. Danoun, L. J. Gooßen, Angew. Chem. Int. Ed. 2013, 52, 6704; Angew. Chem. 2013, 125, 6836.
- 7
- 7aM. Catellani, L. Ferioli, Synthesis 1996, 769;
- 7bM. Catellani, F. Frignani, A. Rangoni, Angew. Chem. Int. Ed. Engl. 1997, 36, 119; Angew. Chem. 1997, 109, 142.
- 8
- 8aM. Catellani, Synlett 2003, 298;
- 8bM. Catellani, E. Motti, N. Della Ca’, Acc. Chem. Res. 2008, 41, 1512;
- 8cA. Martins, B. Mariampillai, M. Lautens, Top. Curr. Chem. 2010, 292, 1;
- 8dX. Sui, R. Zhu, Z. Gu, Synlett 2013, 24, 2023.
- 9For some recent typical reports, see:
- 9aZ. Qureshi, W. Schlundt, M. Lautens, Synthesis 2015, 47, 2446;
- 9bX.-C. Wang, W. Gong, L.-Z. Fang, R.-Y. Zhu, S. Li, K. M. Engle, J.-Q. Yu, Nature 2015, 519, 334;
- 9cZ. Dong, J. Wang, G. Dong, J. Am. Chem. Soc. 2015, 137, 5887;
- 9dH. Zhang, P. Chen, G. Liu, Angew. Chem. Int. Ed. 2014, 53, 10174; Angew. Chem. 2014, 126, 10338;
- 9eM. Sickert, H. Weinstabl, B. Peters, X. Hou, M. Lautens, Angew. Chem. Int. Ed. 2014, 53, 5147; Angew. Chem. 2014, 126, 5247;
- 9fP.-X. Zhou, Y.-Y. Ye, J.-W. Ma, L. Zheng, Q. Tang, Y.-F. Qiu, B. Song, Z.-H. Qiu, P.-F. Xu, Y.-M. Liang, J. Org. Chem. 2014, 79, 6627;
- 9gV. Narbonne, P. Retailleau, G. Maestri, M. Malacria, Org. Lett. 2014, 16, 628;
- 9hL. Jiao, T. Bach, Angew. Chem. Int. Ed. 2013, 52, 6080; Angew. Chem. 2013, 125, 6196;
- 9iX. Sui, R. Zhu, G. Li, X. Ma, Z. Gu, J. Am. Chem. Soc. 2013, 135, 9318;
- 9jH. Weinstabl, M. Suhartono, Z. Qureshi, M. Lautens, Angew. Chem. Int. Ed. 2013, 52, 5305; Angew. Chem. 2013, 125, 5413;
- 9kL. Jiao, E. Herdtweck, T. Bach, J. Am. Chem. Soc. 2012, 134, 14563;
- 9lH. Liu, M. El-Salfiti, M. Lautens, Angew. Chem. Int. Ed. 2012, 51, 9846; Angew. Chem. 2012, 124, 9984;
- 9mH. Liu, M. Ei-Salfiti, D. I. Chai, J. Auffret, M. Lautens, Org. Lett. 2012, 14, 3648;
- 9nL. Jiao, T. Bach, J. Am. Chem. Soc. 2011, 133, 12990;
- 9oG. Maestri, E. Motti, N. Della Ca’, M. Malacria, E. Derat, M. Catellani, J. Am. Chem. Soc. 2011, 133, 8574;
- 9pD. I. Chai, P. Thansandote, M. Lautens, Chem. Eur. J. 2011, 17, 8175;
- 9qM.-H. Larraufie, G. Maestri, A. Beaume, E. Derat, C. Ollivier, L. Fensterbank, C. Courillon, E. Lacote, M. Catellani, M. Malacria, Angew. Chem. Int. Ed. 2011, 50, 12253; Angew. Chem. 2011, 123, 12461;
- 9rM. Blanchot, D. A. Candito, F. Larnaud, M. Lautens, Org. Lett. 2011, 13, 1486;
- 9sA. Martins, D. A. Candito, M. Lautens, Org. Lett. 2010, 12, 5186;
- 9tD. A. Candito, M. Lautens, Org. Lett. 2010, 12, 3312;
- 9uR. Ferraccioli, D. Carenzi, E. Motti, M. Catellani, J. Am. Chem. Soc. 2006, 128, 722.
- 10
- 10aZ. Dong, G. Dong, J. Am. Chem. Soc. 2013, 135, 18350;
- 10bZ.-Y. Chen, C.-Q. Ye, H. Zhu, X.-P. Zeng, J.-J. Yuan, Chem. Eur. J. 2014, 20, 4237;
- 10cC. Ye, H. Zhu, Z. Chen, J. Org. Chem. 2014, 79, 8900;
- 10dH. Shi, D. J. Babinski, T. Ritter, J. Am. Chem. Soc. 2015, 137, 3775;
- 10eF. Sun, Z. Gu, Org. Lett. 2015, 17, 2222.
- 11G. R. Krow, Org. React. 1993, 43, 251.
- 12CCDC 1412197 (3 a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
- 13A transmetallation pathway by dimetallic intermediates was also possible:
- 13aD. J. Cárdenas, B. Martín-Matute, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 5033;
- 13bB. Martín-Matute, C. Mateo, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2001, 7, 2341. See also Ref. [9o].
10.1002/1521-3765(20010601)7:11<2341::AID-CHEM23410>3.0.CO;2-S CAS PubMed Web of Science® Google Scholar
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