Chinese Journal of Organic Chemistry >
Recent Progress in the Research of Acetone in Coupling Reactions
Received date: 2016-07-28
Revised date: 2016-09-15
Online published: 2016-10-09
Supported by
Project supported by the National Natural Science Foundationof China (No. 21572094).
Acetone is the simplest ketone, which has the typical reaction of ketones. In this paper, the recent development centering the coupling reactions of acetone including the formation of carbon-carbon, carbon-heteroatom bonds and the discussion of reaction mechanism, is reviewed.
Key words: acetone; coupling reaction; reaction mechanism
Shen Xuqian , Cao Xihan , Zheng Wanbin , Yang Jun , Shi Yongsen , Hu Jingang , Wu Xiangmei , Yan Guobing . Recent Progress in the Research of Acetone in Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2017 , 37(2) : 349 -355 . DOI: 10.6023/cjoc201607043
[1] (a) Pan, J.; Wang, Y.; Chen, S.; Zhang, X.; Wang Y.; Zhou, Z. Tetrahedron 2016, 72, 240.
(b) Wang, F.; Liu, Y.; Qi, Z.; Dai, W.; Li, X. Tetrahedron Lett. 2014, 55, 6399.
(c) Lu, A.; Wu, R.; Wang, Y.; Wu, G.; Zhou, Z.; Fang, J.; Tang, C. J. Org. Chem. 2011, 76, 3872.
(d) Onodera, G.; Matsumoto, H.; Nishibayashi, Y.; Uemura, S. Organometallics 2005, 24, 5799.
(e) Özkar, S.; Finke, R. G. J. Am. Chem. Soc. 2005, 127, 4800.
(f) Noland, W. E.; Konkel, M. J.; Konkel, L. C.; Pearce, B. C. J. Org. Chem. 1996, 61, 451.
[2] For selected applications, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
(b) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
(c) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
(d) Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082.
(e) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236.
[3] (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
(b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
(c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740.
[4] (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
(b) Shao, Z.; Zhang, H. Chin. J. Org. Chem. 2005, 25, 282.
(c) Gong, J. F.; Xu, C.; Wu, Y. J. Prog. Chem. 2006, 18, 752.
[5] (a) Chobanian, H. R.; Liu, P.; Chioda, M. D.; Guo, Y.; Lin, L. S. Tetrahedron Lett. 2007, 48, 1213.
(b) Su, W. P.; Raders, S.; Verkade, J. G.; Liao, X. B.; Hartwig, J. F. Angew. Chem., Int. Ed. 2006, 45, 5852.
(c) Liu, P.; Lanza, Jr., T. J.; Jewell, J. P.; Jones, C. P.; Hagmann, W. K.; Lin, L. S. Tetrahedron Lett. 2003, 44, 8869.
(d) Kosugi, M.; Suzuki, M.; Hagiwara, I.; Goto, K.; Saitoh, K.; Migita, T. Chem. Lett. 1982, 939.
[6] Hesp, K. D.; Lundgren, R. J.; Stradiotto, M. J. Am. Chem. Soc. 2011, 133, 5194.
[7] Alsabeh, P. G.; Stradiotto, M. Angew. Chem., Int. Ed. 2013, 52, 1.
[8] Rotta-Loria, N. L.; Borzenko, A.; Alsabeh, P. G.; Lavery, C. B.; Stradiotto, M. Adv. Synth. Catal. 2015, 357, 100.
[9] Ackermann, L.; Mehta, V. P. Chem. Eur. J. 2012, 18, 10230.
[10] Li, P.; Lü, B.; Fu, C.; Ma, S. Adv. Synth. Catal. 2013, 355, 1255.
[11] (a) Cartney, D.; Guiry, J. P. Chem. Soc. Rev. 2011, 40, 5122.
(b) Ana, R.; Pathak, T. P.; Sigman, M. Chem. Rev. 2011, 111, 1417.
[12] Gäbler, C.; Korb, M.; Schaarschmidt, D.; Hildebrandt, A.; Lang, H.; Adv. Synth. Catal. 2014, 356, 2979.
[13] (a) MacQueen, P. M.; Chisholm, A. J.; Hargreaves, B. K. V.; Stradiotto, M. Chem. Eur. J. 2015, 21, 11006.
(b) Schranck, J.; Rotzler, J. Org. Process Res. Dev. 2015, 19, 1936.
[14] Fu, W. C.; So, C. M.; Chow, W. K.; Yuen, O. Y.; Kwong, F. Y. Org. Lett. 2015, 17, 4612.
[15] Schranck, J.; Tlili, A.; Alsabeh, P. G.; Neumann, H.; Stradiotto, M.; Beller, M. Chem. Eur. J. 2013, 19, 12624.
[16] For selective reviews, see: (a) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
(b) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
(c) Gansäuer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771.
(d) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94.
(e) Studer, A. Chem. Soc. Rev. 2004, 33, 263.
(f) Brown, S. S.; Stutz, J. Chem. Soc. Rev. 2012, 41, 6405.
(g) zirakis, M. D.; Orfanopoulos, M. Chem. Rev. 2013, 113, 5262. (h) Dénès, F.; Schiesser, C. H.; Renaud, P. Chem. Soc. Rev. 2013, 42, 7900.
[17] (a) Norrish, R. G.; Bond, C. H. Nature 1936, 138, 1016.
(b) Büchi, G.; Inman, C. G.; Lipinsky, E. S. J. Am. Chem. Soc. 1954, 76, 4327.
(c) Nau, W. M.; Cozens, F. L.; Scaiano, J. C. J. Am. Chem. Soc. 1996, 118, 2275.
(d) Reusch, W. J. Org. Chem. 1962, 27, 1882.
(e) Majerski, K. M.; Pavlovi?, D.; Kulyk, M. Š. J. Org. Chem. 1993, 58, 252.
(f) Chung, W.-S.; Ho, C.-C. Chem. Commun. 1997, 317.
(g) Toltl, N. P.; Leigh, W. J. Organometallics 1996, 15, 2554.
(h) Ghandi, K.; Addison-Jones, B.; Brodovitch, J.-C.; McCollum, B. M.; McKenzie, I.; Percival, P. W. J. Am. Chem. Soc. 2003, 125, 9594.
(i) Shiraishi, Y.; Tsukamoto, D.; Hirai, T. Org. Lett. 2008, 10, 3117.
(j) Tsukamoto, D.; Shiraishi, Y.; Hirai, T. J. Org. Chem. 2010, 75, 1450.
[18] Schweitzer-Chaput, B.; Demaerel, B. J.; Engler, H.; Klussmann, M. Angew. Chem., Int. Ed. 2014, 53, 8737.
[19] (a) Xia, X.-F.; Zhu, S-L.; Zeng, M.; Gu, Z.; Wang, H.; Li, W. Tetrahedron 2015, 71, 6099.
(b) oess, E.; Karanestora1, S.; Bosnidou1, A.-E.; Schweitzer-haput, B.; Hasenbeck, M.; Klussmann, M. Synlett 2015, 1973.
[20] Chu, X.-Q.; Meng, H.; Zi, Y.; Xu, X.-P.; Ji, S.-J. Chem. Eur. J. 2014, 20, 17198.
[21] Zhu, L.; Chen, H.; Wang, Z.; Li, C. Org. Chem. Front. 2014, 1, 1299.
[22] Lan, X.-W.; Wang, N.-X.; Zhang, W.; Wen, J.-L.; Bai, C.-B.; Xing, Y.; Li, Y.-H. Org. Lett. 2015, 17, 4460.
[23] Wang, C.; Lei, S.; Cao, H.; Qiu, S.; Liu, J.; Deng, H.; Yan, C. J. Org. Chem. 2015, 80, 12725.
[24] Yan, G.; Borah, A. J.; Wang, L.; Pan, Z.; Chen, C.; Shen, X.; Wu, X. Tetrahedron Lett. 2015, 56, 4305.
[25] Shen, X.; Borah, A. J.; Cao, X.; Pan, W.; Yan, G.; Wu, X. Tetrahedron Lett. 2015, 56, 6484.
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