Direct Vinylation of Activated Methines by a Vinylsulfonium Salt

Page: [389 - 394] Pages: 6

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Abstract

Vinylation of activated methines is a synthetically useful and challenging transformation. Traditional methods for this transformation always encounter multiple steps, limited generality and/or handling gaseous substrates. Herein, we report by using diphenyl(vinyl)sulfonium triflate as a vinylation component, a one-step direct vinylation of activated methines can be realized under mild conditions. This reaction, compatible with several kinds of activated methines, can lead to the construction of vinylated quaternary carbon centers concisely.

Keywords: Vinylation, Activated methine, Vinylsulfonium, Tandem Reaction, quaternary carbon center, cascade reaction

Graphical Abstract

[1]
a) Sengupta, S.; Pramanik, A.; Ghosh, A.; Bhattacharyya, M. BMC Microbiol. 2015, 15, 170/1-170/16..;
b) Farr, S.J.; Turanin, J.; Hawley, R.; Schuster, J.A. Patent WO 2009134336 A1 20091105, 2009.
[2]
a) Xu, P. Huang. Z. Nat. Chem., 2021, 13(7), 634-642.
[http://dx.doi.org/10.1038/s41557-021-00715-0] [PMID: 34112991];
b) Li, Z.X.; Wang, M.Y.; Shi, Z.Z. Angew. Chem. Int. Ed., 2021, 60, 186-190.;
c) Enoki, J.; Mügge, C.; Tischler, D.; Miyamoto, K.; Kourist, R. Chemistry, 2019, 25(19), 5071-5076.
[http://dx.doi.org/10.1002/chem.201806339] [PMID: 30702787]
[3]
a) Haraldsson, T.; Mikaelsson, H.; Hansson, J.; Carlborg, C.F. Patent WO 2022090424 A1 20220505,, 2022.;
b) Dogra, K.; Moloy, K.G.; Bauer, R.D.; Williamson, D.T. Patent WO 2009073702 A1 20090611,, 2009.
[4]
Zhou, X.; Xu, Y.; Dong, G. J. Am. Chem. Soc., 2021, 143(48), 20042-20048.
[http://dx.doi.org/10.1021/jacs.1c09587] [PMID: 34807585]
[5]
Nakamura, M.; Endo, K.; Nakamura, E. Org. Lett., 2005, 7(15), 3279-3281.
[http://dx.doi.org/10.1021/ol051057z] [PMID: 16018640]
[6]
Mondal, M.; Chen, S.; Kerrigan, N. Molecules, 2018, 23(4), 738-767.
[http://dx.doi.org/10.3390/molecules23040738] [PMID: 29570624]
[7]
a) McGarrigle, E.M.; Fritz, S.P.; Favereau, L.; Yar, M.; Aggarwal, V.K. Org. Lett., 2011, 13(12), 3060-3063.
[http://dx.doi.org/10.1021/ol2009472] [PMID: 21591804];
b) Xie, C.; Han, D.; Hu, Y.; Liu, J.; Xie, T. Tetrahedron Lett., 2010, 51(40), 5238-5241. http://dx.doi.org/10.1016/j.tetlet.2010.07.108;
c) Yar, M.; McGarrigle, E.M.; Aggarwal, V.K. Org. Lett., 2009, 11(2), 257-260.
[http://dx.doi.org/10.1021/ol8023727] [PMID: 19072319];
d) Yar, M.; McGarrigle, E.M.; Aggarwal, V.K. Angew. Chem. Int. Ed., 2008, 47(20), 3784-3786.
[http://dx.doi.org/10.1002/anie.200800373] [PMID: 18404756]
[8]
a) Unthank, M.G.; Tavassoli, B.; Aggarwal, V.K. Org. Lett., 2008, 10(7), 1501-1504.
[http://dx.doi.org/10.1021/ol800318h] [PMID: 18336037];
b) Unthank, M.G.; Hussain, N.; Aggarwal, V.K. Angew. Chem. Int. Ed., 2006, 45(42), 7066-7069.
[http://dx.doi.org/10.1002/anie.200602782] [PMID: 17009383];
c) Mukaiyama, T.; Yamanaka, H.; Yamane, Y. Heterocycles, 2004, 63(12), 2813-2826.
[http://dx.doi.org/10.3987/COM-04-10232];
d) Matsuo, J.; Yamanaka, H.; Kawana, A.; Mukaiyama, T. Chem. Lett., 2003, 32(4), 392-393. http://dx.doi.org/10.1246/cl.2003.392;
e) Kim, K.; Jimenez, L.S. Tetrahedron Asymmetry, 2001, 12(7), 999-1005. http://dx.doi.org/10.1016/S0957-4166(01)00170-7;
f) Wang, Y.; Zhang, W.; Colandrea, V.J.; Jimenez, L.S. Tetrahedron, 1999, 55(35), 10659-10672.
[http://dx.doi.org/10.1016/S0040-4020(99)00605-5]
[9]
a) Srogl, J.; Allred, G.D.; Liebeskind, L.S. J. Am. Chem. Soc., 1997, 119(50), 12376-12377. http://dx.doi.org/10.1021/ja9726926;
b) Lin, H.; Dong, X.; Li, Y.; Shen, Q.; Lu, L. Eur. J. Org. Chem., 2012, 2012(25), 4675-4679. http://dx.doi.org/10.1002/ejoc.201200758;
c) Aukland, M.H.; Talbot, F.J.T.; Fernández-Salas, J.A.; Ball, M.; Pulis, A.P.; Procter, D.J. Angew. Chem. Int. Ed., 2018, 57(31), 9785-9789.
[http://dx.doi.org/10.1002/anie.201805396] [PMID: 29882623];
d) Chen, J.; Li, J.; Plutschack, M.B.; Berger, F.; Ritter, T. Angew. Chem. Int. Ed., 2020, 59(14), 5616-5620.
[http://dx.doi.org/10.1002/anie.201914215] [PMID: 31782968]
[10]
Zhang, Y.L.; Yang, L.; Wu, J.; Zhu, C.; Wang, P. Org. Lett., 2020, 22(19), 7768-7772.
[http://dx.doi.org/10.1021/acs.orglett.0c03074] [PMID: 32966742]
[11]
Lin, H.; Shen, Q.; Lu, L. J. Org. Chem., 2011, 76(18), 7359-7369.
[http://dx.doi.org/10.1021/jo2009033] [PMID: 21797270]
[12]
a) Zhao, Y.R.; Li, L.; Xu, G.Y. Xuan. J. Adv. Synth. Catal., 2022, 364(3), 506-511. http://dx.doi.org/10.1002/adsc.202101144;
b) Bychek, R.M.; Levterov, V.V.; Sadkova, I.V.; Tolmachev, A.A.; Mykhailiuk, P.K. Chemistry, 2018, 24(47), 12291-12297.
[http://dx.doi.org/10.1002/chem.201705708] [PMID: 29419903];
c) Hagiwara, H.; Sato, K.; Nishino, D.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1, 2001, 22(22), 2946-2957. http://dx.doi.org/10.1039/b107180g;
d) Hagiwara, H.; Sato, K.; Suzuki, T.; Ando, M. Tetrahedron Lett., 1997, 38(12), 2103-2106.
[http://dx.doi.org/10.1016/S0040-4039(97)00317-1]