Chinese Journal of Organic Chemistry >
Diacetoxyiodobenzene Promoted Chlorination of Silyl Enol Ether of Aryl Ketones
Received date: 2015-11-19
Revised date: 2015-12-30
Online published: 2016-02-01
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21362033, 21502154).
A series of α-chloroketones were obtained from silyl enol ethers of aryl ketones using trimethylchlorosilane as chlorine source and diacetoxyiodobenzene as promoter. The reaction occurs under mild condition yielding the product in moderate to good yields, and has the potential possibility for the synthesis of α-bromoketone by using trimethyl bromosilane as bromine source.
Chen Xiaowei , Chong Siying , Du Ganggang , Huang Danfeng , Wang Kehu , Su Yingpeng , Hu Yulai . Diacetoxyiodobenzene Promoted Chlorination of Silyl Enol Ether of Aryl Ketones[J]. Chinese Journal of Organic Chemistry, 2016 , 36(5) : 1028 -1033 . DOI: 10.6023/cjoc201511041
[1] (a) De Kimpe, N.; Verhé, R.; Patai, S. The Chemistry of α-haloketones, α-haloaldehydes, and α-haloimines, John Wiley & Sons Inc, Chichester, 1988.
(b) Yasuda, M.; Tsuji, S.; Shigeyoshi, Y.; Baba, A. J. Am. Chem. Soc. 2002, 124, 7440.
(c) Hamada, T.; Torii, T.; Izawa, K.; Ikariya, T. Tetrahedron 2004, 60, 7411.
(d) Adamo, M. F. A.; Adlington, R. M.; Baldwin, J. E.; Day, A. L. Tetrahedron 2004, 60, 841.
(e) Tanis, S. P.; Evans, B. R.; Nieman, J. A.; Parker, T. T.; Taylor, W. D.; Heasley, S. E.; Herrinton, P. M.; Perrault, W. R.; Hohler, R. A.; Dolak, L. A.; Hester, M. R.; Seest, E. P. Tetrahedron: Asymmetry 2006, 17, 2154.
(f) Kojima, S.; Suzuki, M.; Watanabe, A.; Ohkata, K. Tetrahedron Lett. 2006, 47, 9061.
(g) Wei, Q.-L.; Zhang, S.-S.; Gao, J.; Li, W.-h.; Xu, L.-Z.; Yu, Z.-G. Bioorg. Med. Chem. 2006, 14, 7146.
(h) Gerby, B.; Boumendjel, A.; Blanc, M.; Bringuier, P. P.; Champelovier, P.; Fortuné, A.; Ronot, X.; Boutonnat, J. Bioorg. Med. Chem. Lett. 2007, 17, 208.
(i) Yu, L.-T.; Ho, M.-T.; Chang, C.-Y.; Yang, T.-K. Tetrahedron: Asymmetry 2007, 18, 949.
(j) Malkov, A. V.; Ston?ius, S.; Ko?ovský, P. Angew. Chem., Int. Ed. 2007, 46, 3722.
(k) Fan, X.; Song, Y.-L.; Long, Y.-Q. Org. Process Res. Dev. 2008, 12, 69.
(l) Britton, R.; Kang, B. Nat. Prod. Rep. 2013, 30, 227.
[2] (a) Pearson, D. E.; Pope, H. W.; Hargrove, W. W. Org. Synth. 1973, V, 117.
(b) Diwu, Z.; Beachdel, C.; Klaubert, D. H. Tetrahedron Lett. 1998, 39, 4987.
[3] (a) Kosower, E. M.; Cole, W. J.; Wu, G. S.; Cardy, D. E.; Meisters, G. J. Org. Chem. 1963, 28, 630.
(b) King, L. C.; Ostrum, G. K. J. Org. Chem. 1964, 29, 3459.
[4] (a) Adhikari, M. V.; Samant, S. D. Ultrason. Sonochem. 2002, 9, 107.
(b) Lee, J. C.; Bae, Y. H.; Chang, S.-K. Bull. Korean Chem. Soc. 2003, 24, 407.
(c) Meshram, H. M.; Reddy, P. N.; Sadashiv, K.; Yadav, J. S. Tetrahedron Lett. 2005, 46, 623.
(d) Chan Lee, J.; Jung Park, H. Synth. Commun. 2007, 37, 87.
[5] (a) Reuss, R. H.; Hassner, A. J. Org. Chem. 1974, 39, 1785.
(b) Blanco, L.; Amice, P.; Conia, J. M. Synthesis 1976, 194.
(c) Olah, G. A.; Ohannesian, L.; Arvanaghi, M.; Prakash, G. K. S. J. Org. Chem. 1984, 49, 2032.
(d) Ram, R. N.; Manoj, T. P. J. Org. Chem. 2008, 73, 5633.
(e) Jing, Y.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 4932.
[6] Mizar, P.; Wirth, T. Angew. Chem., Int. Ed. 2014, 53, 5993.
[7] (a) Wirth, T. Topics in Current Chemistry 2003, 224, 1~248.
(b) Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds, John Wiley & Sons, Chichester, 2013.
(c) Chen, J.; Qu, H. M.; Peng, J.; Chen, C. Chin. J. Org. Chem. 2015, 35, 937 (in Chinese).
(陈静, 曲红梅, 彭静, 陈超, 有机化学, 2015, 35, 937.)
[8] (a) Moriarty, R. M.; Hu, H.; Gupta, S. C. Tetrahedron Lett. 1981, 22, 1283.
(b) Koser, G. F.; Relenyi, A. G.; Kalos, A. N.; Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1982, 47, 2487.
(c) Merritt, E. A.; Olofsson, B. Synthesis 2011, 517.
(d) Song, A. R.; Zhang, C. Acta Chim. Sinica 2015, 73, 1002 (in Chinese).
(宋爱茹, 张弛, 化学学报, 2015, 73, 1002.)
[9] (a) Akula, R.; Galligan, M.; Ibrahim, H. Chem. Commun. 2009, 6991.
(b) Ibrahim, H.; Akula, R.; Galligan, M. Synthesis 2011, 347.
(c) Galligan, M. J.; Akula, R.; Ibrahim, H. Org. Lett. 2014, 16, 600.
[10] (a) Hara, S.; Sekiguchi, M.; Ohmori, A.; Fukuhara, T.; Yoneda, N. Chem. Commun. 1996, 1899.
(b) Jia, Z.; Galvez, E.; Sebastian, R. M.; Pleixats, R.; Alvarez-Larena, A.; Martin, E.; Vallribera, A.; Shafir, A. Angew. Chem., Int. Ed. 2014, 53, 11298.
(c) Narayan, R.; Manna, S.; Antonchick, A. P. Synlett 2015, 1785.
[11] Xu, Z.; Zhang, D.; Zou, X. Synth. Commun. 2006, 36, 255.
[12] Paul, S.; Gupta, V.; Gupta, R.; Loupy, A. Tetrahedron Lett. 2003, 44, 439.
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