Facile Access to β-Ketosulfones via Mn-Mediated Reductive Coupling of α-Bromoketones with Sulfonyl Chlorides
- Corresponding author: Chen Rongshun, rongshunchen@njau.edu.cn Zhu Yingguang, ygzhu@njau.edu.cn
Citation:
Chen Zhen, Guo Kang, Chen Rongshun, Gu Chen, Zhou Huating, Zhu Yingguang. Facile Access to β-Ketosulfones via Mn-Mediated Reductive Coupling of α-Bromoketones with Sulfonyl Chlorides[J]. Chinese Journal of Organic Chemistry,
;2018, 38(4): 963-968.
doi:
10.6023/cjoc201710027
For selected exam. p. les, see: (a) Napier, C. ; Stewart, M. ; Melrose, H. ; Hopkins, B. ; McHarg, A. ; Wallis, R. Eur. J. Pharmacol. 1999, 375, 61.
(b) Petrov, K. G. ; Zhang, Y. ; Carter, M. ; Cockerill. G. S. ; Dickerson, S. ; Gauthier, C. A. ; Guo, Y. ; Mook, R. A. ; Rusnak, D. W. ; Walker, A. L. ; Wood, E. R. ; Lackey, K. E. Bioorg. Med. Chem. Lett. 2006, 16, 4686.
(c) Ma, M. ; Cheng, Y. ; Xu, Z. ; Xu, P. ; Qu, H. ; Fang, Y. ; Wen, L. Eur. J. Med. Chem. 2007, 42, 93.
(d) Jiang, J. ; Zou, H. ; Yi, N. ; Wang, R. ; Zhang, H. ; Lan, L. ; Xiang, J. Chin. J. Chem. 2016, 34, 1245.
(a) Wolf, W. M. J. Mol. Struct. 1999, 474, 113.
(b) Curti, C. ; Laget, M. ; Carle, A. O. ; Gellis, A. ; Vanelle, P. Eur. J. Med. Chem. 2007, 42, 880.
(c) Xiang, J. ; Ipek, M. ; Suri, V. ; Tam, M. ; Xing, Y. ; Huang, N. ; Zhang, Y. ; Tobin, J. ; Mansour, T. S. ; McKew, J. Bioorg. Med. Chem. 2007, 15, 4396.
(a) Bertus, P. ; Phansavath, P. ; Ratovelomanana-Vidal, V. ; Genêt, J. -P. ; Touati, A. R. ; Homri, T. ; Hassine, B. B. Tetrahedron: Asymmetry 1999, 10, 1369.
(b) Huang, X. ; Zhao, M. ; Li, N. ; Li, H. ; Li, J. ; Wang, X. Chin. J. Chem. 2014, 32, 803.
Sengupta, S.; Sarma, D. S.; Mondal, S. Tetrahedron:Asymmetry 1998, 9, 2311.
doi: 10.1016/S0957-4166(98)00235-3
Suryakiran, N.; Reddy, T. S.; Suresh, V.; Lakshman, M.; Venkateswarlu, Y. Tetrahedron Lett. 2006, 47, 4319.
doi: 10.1016/j.tetlet.2006.04.123
(a) Bartlett, P. A. ; Green, Ⅲ, F. R. ; Rose, E. H. J. Am. Chem. Soc. 1978, 100, 4852.
(b) Ihara, M. ; Suzuki, S. ; Taniguchi, T. ; Tokunaga, Y. ; Fukumoto, K. Tetrahedron 1995, 51, 9873.
Baldwin, J. E.; Adlington, R. M.; Crouch, N. P.; Hill, R. L.; Laffey, T. G. Tetrahedron Lett. 1995, 36, 7925.
doi: 10.1016/0040-4039(95)01643-V
Swenson, R. E.; Sowin, T. J.; Zhang, H. Q. J. Org. Chem. 2002, 67, 9182.
doi: 10.1021/jo0203387
Marco, J. L. J. Org. Chem. 1997, 62, 6575.
doi: 10.1021/jo9705982
(a) Vennstra, G. E. ; Zwaneburg, B. Synthesis 1975, 519.
(b) Xie, Y. -Y., Chen, Z. -C. Synth. Commun. 2001, 31, 3145.
(a) Lu, Q. ; Zhang, J. ; Zhao, G. ; Qi, Y. ; Wang, H. ; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481.
(b) Wang, H. ; Wang, G. ; Lu, Q. ; Chiang, C. -W. ; Peng, P. ; Zhou, J. ; Lei, A. Chem. Eur. J. 2016, 22, 14489.
Wei, W.; Liu, C.; Yang, D.; Wen, J.; You, J.; Suo, Y.; Wang, H. Chem. Commun. 2013, 49, 10239.
doi: 10.1039/c3cc45803b
Wei, W.; Wen, J.; Yang, D.; Wu, M.; You, J.; Wang, H. Org. Biomol. Chem. 2014, 12, 7678.
doi: 10.1039/C4OB01369G
Yang, D.; Huang B.; Wei, W.; Li, J.; Lin, G.; Liu, Y.; Ding, J.; Sun, P.; Wang, H. Green Chem. 2016, 18, 5630.
doi: 10.1039/C6GC01403H
Singh, A. K.; Chawla, R.; Keshari, T.; Yadav, V. K.; Yadav, L. D. S. Org. Biomol. Chem. 2014, 12, 8550.
doi: 10.1039/C4OB00776J
Singh, A. K.; Chawla, R.; Yadav, L. D. S. Tetrahedron Lett. 2014, 55, 4742.
doi: 10.1016/j.tetlet.2014.06.086
Jiang, Y.; Loh, T.-P. Chem. Sci. 2014, 5, 4939.
doi: 10.1039/C4SC01901F
Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem., Int. Ed. 2014, 53, 4205.
doi: 10.1002/anie.201311217
For selected reviews on transition metal-catalyzed carbon-carbon bond-forming reductive coupling with stoichiometric reductants such as Mn, see: (a) Knappke, C. E. I. ; Grupe, S. ; G rtner, D. ; Corpet, M. ; Gosmini, C. ; Jacobi von Wangelin, A. Chem. -Eur. J. 2014, 20, 6828.
(b) Moragas, T. ; Correa, A. ; Martin, R. Chem. -Eur. J. 2014, 20, 8242.
(c) Weix, D. J. Acc. Chem. Res. 2015, 48, 1767.
(d) Wang, X. ; Dai, Y. ; Gong, H. Top. Curr. Chem. 2016, 374, 43.
(a) Ye, Y. ; Zhou, Q. ; Zheng, R. ; Jiang, H. ; Chen, R. ; Zhang, Y. Appl. Organomet. Chem. 2011, 25, 331.
(b) Xia, Y. ; Chen, X. ; Qu, L. ; Sun, K. ; Xia, X. ; Fu, W. ; Chen, X. ; Yang, Y. ; Zhao, Y. ; Li, C. Asian J. Org. Chem. 2016, 5, 878.
(c) Sun, X. ; Wang, L. ; Zhang, Y. Synth. Commun. 1998, 28, 1785.
(d) Srinivas, K. ; Dubey, P. K. Synth. Commun. 2011, 41, 1584.
(e) Saikia, P. ; Laskar, D. D. ; Prajapati, D. ; Sandhu, J. S. Chem. Lett. 2001, 512.
(f) Fu, Y. ; Xu, Q. -S. ; Li, Q. -Z. ; Du, Z. ; Wang, K. -H. ; Huang, D. ; Hu, Y. Org. Biomol. Chem. 2017, 15, 2841.
Naeimi, H.; Nazifi, Z. S. Russ. Chem. Bull. 2015, 64, 1814.
doi: 10.1007/s11172-015-1076-2
Compared to other additives such as NaI and TBAI, I2 exhibited better promoting effect and gave a higher yield. It is likely that I2 has better solubility than NaI and TBAI in DMA at room temperature. The exact reason for this is unclear at the moment. Besides the possible halogen exchange process, I2 might also activate the surface of manganese to promote the reaction.
Chen, J.; Liu, D.; Butt, N.; Li, C.; Fan, D.; Liu, Y.; Zhang, W. Angew. Chem., Int. Ed. 2013, 52, 11632.
doi: 10.1002/anie.201306231
Pravst, I.; Zupan, M.; Stavber, S. Tetrahedron 2008, 64, 5191.
doi: 10.1016/j.tet.2008.03.048
Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem., Int. Ed. 2014, 53, 4205.
doi: 10.1002/anie.201311217
Kumar, A.; Muthyala, M. K. Tetrahedron Lett. 2011, 52, 5368.
doi: 10.1016/j.tetlet.2011.08.035
Rothberg, I.; Sundoro, B.; Bslanikas, G.; Kirsch, S. J. Org. Chem. 1983, 48, 4345.
doi: 10.1021/jo00171a037
Weinstock, J.; Pearson, R. G.; Bordwell, F. G. J. Am. Chem. Soc. 1956, 78, 3468.
doi: 10.1021/ja01595a055
Garcı́a-Ruano, J. L.; Rumbero, A. Tetrahedron:Asymmetry 1999, 10, 4427.
doi: 10.1016/S0957-4166(99)00467-X
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