Recent Progress in the Addition Reaction of Electron-Rich Alkynes and Carboxylic Acids

doi:10.6023/cjoc202003045

Abstract

Electron-rich alkynes, in which an electron-donating atom or group is attached to the triple bond, have been widely used as versatile building blocks in organic synthesis, due to their unique chemical reactivity. As an important part of electron-rich alkyne chemistry, the addition reaction between electron-rich alkynes and carboxylic acids received considerable attention these years, and various investigations and advances have been reported. The progress of addition reactions between electron-rich alkynes and carboxylic acids is summarized, and the future perspective is prospected.

Key words: electron-rich alkyne, carboxylic acid, addition reaction, hydro-acyloxylation

Cite this article

Zeng Linwei, Cui Sunliang. Recent Progress in the Addition Reaction of Electron-Rich Alkynes and Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2353-2373.

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References

[1] (a) Janousek, Z.; Viehe, H. G.; Collard, J. Angew. Chem., Int. Ed. 1972, 11, 917.
(b) Tu, Y.; Zeng, X.; Wang, H.; Zhao, J. Org. Lett. 2018, 20, 280.
(c) Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2009, 48, 4381.
(d) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L. C.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
(e) Mansfield, S. J.; Campbell, C. D.; Jones, M. W.; Anderson, E. A. Chem. Commun. 2015, 51, 3316.
(f) Souto, J. A.; Becker, P.; Iglesias, A.; Muniz, K. J. Am. Chem. Soc. 2012, 134, 15505.
(g) Zhang, X. J.; Zhang, Y. S.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L. C.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170.
(h) Jouvin, K.; Coste, A.; Bayle, A.; Legrand, F.; Karthikeyan, G.; Tadiparthi, K.; Evano, G. Organometallics 2012, 31, 7933.
(i) Jouvin, K.; Bayle, A.; Legrand, F.; Evano, G. Org. Lett. 2012, 14, 1652.
(j) Kanemoto, K.; Yoshida, S.; Hosoya, T. Org. Lett. 2019, 21, 3172.
(k) Kiefer, G.; Riedel, T.; Dyson, P. J.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2015, 54, 302.
(l) Pena, J.; Talavera, G.; Waldecker, B.; Alcarazo, M. Chem.-Eur. J. 2017, 23, 75.
[2] (a) Wang, X. N.; Yeom, H. S.; Fang, L. C.; He, S. H.; Ma, Z. X.; Kedrowski, B. L.; Hsung, R. P. Acc. Chem. Res. 2014, 47, 560.
(b) Pan, F.; Shu, C.; Ye, L. W. Org. Biomol. Chem. 2016, 14, 9456.
(c) Wang, Y.; Song, L. J.; Zhang, X. H.; Sun, J. W. Angew. Chem., Int. Ed. 2016, 55, 9704.
(d) Zhu, C.; Feng, J.; Zhang, J. Chin. J. Org. Chem. 2017, 37, 1165(in Chinese). (朱超泽, 冯见君, 张俊良, 有机化学, 2017, 37, 1165.)
(e) Liu, J.; Chakraborty, P.; Zhang, H.; Zhong, L.; Wang, Z.; Huang, X. ACS Catal. 2019, 9, 2610.
[3] (a) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095.
(b) Banerjee, B.; Litvinov, D. N.; Kang, J.; Bettale, J. D.; Castle, S. L. Org. Lett. 2010, 12, 2650.
(c) Wang, L.; Lu, C. R.; Yue, Y. N.; Feng, C. Org. Lett. 2019, 21, 3514.
[4] (a) Shen, C.-H.; Li, L.; Zhang, W.; Liu, S.; Shu, C.; Xie, Y.-E.; Yu, Y.-F.; Ye, L.-W. J. Org. Chem. 2014, 79, 9313.
(b) Liu, R. H.; Winston-McPherson, G. N.; Yang, Z. Y.; Zhou, X.; Song, W. Z.; Guzei, I. A.; Xu, X. F.; Tang, W. P. J. Am. Chem. Soc. 2013, 135, 8201.
(c) Davies, P. W.; Cremonesi, A.; Martin, N. Chem. Commun. 2011, 47, 379.
[5] (a) Ding, S. T.; Jia, G. C.; Sun, J. W. Angew. Chem., Int. Ed. 2014, 53, 1877.
(b) Tian, X. H.; Song, L. N.; Rudolph, M.; Rominger, F.; Oeser, T.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2019, 58, 3589.
(c) DeKorver, K. A.; Li, H. Y.; Lohse, A. G.; Hayashi, R.; Lu, Z. J.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064.
(d) Zhou, B.; Li, L.; Zhu, X. Q.; Yan, J. Z.; Guo, Y. L.; Ye, L. W. Angew. Chem., Int. Ed. 2017, 56, 4015.
(e) Zeng, L.; Lai, Z.; Zhang, C.; Xie, H.; Cui, S. Org. Lett. 2020, 22, 2220.
[6] (a) Zhang, W. H.; Ready, J. M. J. Am. Chem. Soc. 2016, 138, 10684.
(b) Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A. Org. Lett. 2005, 7, 1047.
(c) Couty, S.; Liegault, B.; Meyer, C.; Cossy, J. Tetrahedron 2006, 62, 3882.
(d) Couty, S.; Meyer, C.; Cossy, J. Tetrahedron Lett. 2006, 47, 767.
(e) Alayrac, C.; Schollmeyer, D.; Witulski, B. Chem. Commun. 2009, 1464.
[7] (a) Cao, W.; Chen, P.; Wang, L.; Wen, H.; Liu, Y.; Wang, W. S.; Tang, Y. Org. Lett. 2018, 20, 4507.
(b) Compain, G.; Jouvin, K.; Mingot, A. M.; Evano, G.; Marrot, J.; Thibaudeau, S. Chem. Commun. 2012, 48, 5196.
(c) Métayer, B.; Compain, G.; Jouvin, K.; MartinMingot, A.; Bachmann, C.; Marrot, J.; Evano, G.; Thibaudeau, S. J. J. Org. Chem. 2015, 80, 3397.
(d) Zeng, X. J.; Lu, Z. C.; Liu, S. W.; Hammond, G. B.; Xu, B. J. Org. Chem. 2017, 82, 13179.
(e) Li, X.; Sun, Y.; Zhang, L.; Peng, B. Chin. J. Org. Chem. 2016, 36, 2530(in Chinese). (李晓锦, 孙艳, 张磊, 彭勃, 有机化学, 2016, 36, 2530.)
[8] (a) Kanemura, S.; Kondoh, A.; Yasui, H.; Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2008, 81, 506.
(b) Yasui, H.; Yorimitsu, H.; Oshima, K. Chem. Lett. 2008, 37, 40.
(c) Kim, S. W.; Um, T. W.; Shin, S. Chem. Commun. 2017, 53, 2733.
[9] (a) Tolchinskii, S. E.; Dogadina, A. V.; Maretina, I. A.; Petrov, A. A. Zh. Org. Khim. 1980, 16, 1141.
(b) Yoo, H. J.; Youn, S. W. Org. Lett. 2019, 21, 3422.
[10] (a) Rentsch, C.; Slongo, M.; Stadelma, W.; Neuensch, M. Chimia 1973, 27, 70.
(b) Zhang, Y.; DeKorver, K. A.; Lohse, A. G.; Zhang, Y. S.; Huang, J.; Hsung, R. P. Org. Lett. 2009, 11, 899.
(c) DeKorver, K. A.; Johnson, W. L.; Zhang, Y.; Hsung, R. P.; Dai, H. F.; Deng, J.; Lohse, A. G.; Zhang, Y. S. J. Org. Chem. 2011, 76, 5092.
[11] (a) Bianchini, C.; Meli, A.; Peruzzini, M.; Zanobini, F.; Bruneau, C.; Dixneuf, P. H. Organometallics 1990, 9, 1155.
(b) Chen, J.-F.; Li, C. Org. Lett. 2018, 20, 6719.
(c) Goossen, L. J.; Paetzold, J.; Koley, D. Chem. Commun. 2003, 706.
(d) Hua, R. M.; Tian, X. J. Org. Chem. 2004, 69, 5782.
(e) Jeschke, J.; Gabler, C.; Lang, H. J. Org. Chem. 2016, 81, 476.
(f) Lumbroso, A.; Vautravers, N. R.; Breit, B. Org. Lett. 2010, 12, 5498.
(g) Rotem, M.; Shvo, Y. Organometallics 1983, 2, 1689.
(h) Wang, Y.; Wang, Z.; Li, Y.; Wu, G.; Cao, Z.; Zhang, L. Nat. Commun. 2014, 5, 3470.
(i) Dupuy, S.; Gasperini, D.; Nolan, S. P. ACS Catal. 2015, 5, 6918.
[12] Smith, D. L.; Goundry, W. R. F.; Lam, H. W. Chem. Commun. 2012, 48, 1505.
[13] Xu, S.; Liu, J.; Hu, D.; Bi, X. Green Chem. 2015, 17, 184.
[14] (a) Hu, L.; Xu, S.; Zhao, Z.; Yang, Y.; Peng, Z.; Yang, M.; Wang, C.; Zhao, J. J. Am. Chem. Soc. 2016, 138, 13135.
(b) Hu, L.; Zhao, J. Synlett 2017, 28, 1663.
[15] Yang, J.; Wang, C.; Xu, S.; Zhao, J. Angew. Chem., Int. Ed. 2019, 58, 1382.
[16] Wang, X.; Yang, Y.; Zhao, Y.; Wang, S.; Hu, W.; Li, J.; Wang, Z.; Yang, F.; Zhao, J. J. Org. Chem. 2020, 85, 6188.
[17] Yang, M.; Wang, X.; Zhao, J. ACS Catal. 2020, 10, 5230.
[18] Huang, B.; Zeng, L.; Shen, Y.; Cui, S. Angew. Chem., Int. Ed. 2017, 56, 4565.
[19] Shen, Y.; Huang, B.; Zeng, L.; Cui, S. Org. Lett. 2017, 19, 4616.
[20] (a) Quinone Methides, Ed.:Rokita, S. E., Wiley, New York, 2009.
(b) Yang, B.; Gao, S. Chem. Soc. Rev. 2018, 47, 7926.
[21] Chen, R.; Liu, Y.; Cui, S. Chem. Commun. 2018, 54, 11753.
[22] Shen, Y.; Li, Q.; Xu, G.; Cui, S. Org. Lett. 2018, 20, 5194.
[23] Shen, Y.; Wang, C.; Chen, W.; Cui, S. Org. Chem. Front. 2018, 5, 3574.
[24] (a) Pusterla, I.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 513.
(b) Doll, M. K. H. J. Org. Chem. 1999, 64, 1372.
(c) Gooβen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043.
(d) Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738.
[25] Chen, R.; Zeng, L.; Huang, B.; Shen, Y.; Cui, S. Org. Lett. 2018, 20, 3377.
[26] Habert, L.; Retailleau, P.; Gillaizeau, I. Org. Biomol. Chem. 2018, 16, 7351.
[27] (a) Qin, T.; Cornella, J.; Li, C.; Malins, L. R.; Edwards, J. T.; Kawamura, S.; Maxwell, B. D.; Eastgate, M. D.; Baran, P. S. Science 2016, 352, 801.
(b) Cornella, J.; Edwards, J. T.; Qin, T.; Kawamura, S.; Wang, J.; Pan, C. M.; Gianatassio, R.; Schmidt, M.; Eastgate, M. D.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 2174.
(c) Toriyama, F.; Cornella, J.; Wimmer, L.; Chen, T. G.; Dixon, D. D.; Creech, G.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 11132.
(d) Qin, T.; Malins, L. R.; Edwards, J. T.; Merchant, R. R.; Novak, A. J. E.; Zhong, J. Z.; Mills, R. B.; Yan, M.; Yuan, C.; Eastgate, M. D.; Baran, P. S. Angew. Chem., Int. Ed. 2019, 58, 112.
(e) Qin, T.; Malins, L. R.; Edwards, J. T.; Merchant, R. R.; Novak, A. J. E.; Zhong, J. Z.; Mills, R. B.; Yan, M.; Yuan, C. X.; Eastgate, M. D.; Baran, P. S. Angew. Chem., Int. Ed. 2017, 56, 260.
(f) Edwards, J. T.; Merchant, R. R.; McClymont, K. S.; Knouse, K. W.; Qin, T.; Malins, L. R.; Vokits, B.; Shaw, S. A.; Bao, D. H.; Wei, F. L.; Zhou, T.; Eastgate, M. D.; Baran, P. S. Nature 2017, 545, 213.
[28] Huang, B.; Zeng, L.; Shen, Y.; Cui, S. Chem. Commun. 2017, 53, 11996.
[29] (a) Wasserman, H. H.; Wharton, P. S. J. Am. Chem. Soc. 1960, 82, 661.
(b) Wasserman, H. H.; Wharton, P. S. Tetrahedron 1958, 3, 321.
[30] Kita, Y.; Akai, S.; Yoshigi, M.; Nakajima, Y.; Yasuda, H.; Tamura, Y. Tetrahedron Lett. 1984, 25, 6027.
[31] Kita, Y.; Akai, S.; Ajimura, N.; Yoshigi, M.; Tsugoshi, T.; Yasuda, H.; Tamura, Y. J. Org. Chem. 1986, 51, 4150.
[32] Kita, Y.; Akai, S.; Yamamoto, M.; Taniguchi, M.; Tamura, Y. Synthesis 1989, 334.
[33] Yin, J.; Bai, Y. H.; Mao, M. Y.; Zhu, G. G. J. Org. Chem. 2014, 79, 9179.
[34] Zeng, L.; Huang, B.; Shen, Y.; Cui, S. Org. Lett. 2018, 20, 3460.
[35] (a) Zeng, L.; Lai, Z.; Cui, S. J. Org. Chem. 2018, 83, 14834.
(b) Zeng, L.; Sajiki, H.; Cui, S. Org. Lett. 2019, 21, 6423.
[36] Berger, D.; Neuenschwander, M. Helv. Chim. Acta 1996, 79, 192.
[37] Mishiro, K.; Yushima, Y.; Kunishima, M. J. Org. Chem. 2018, 83, 13595.
[38] (a) Wang, H.; Cheng, Y.; Becker, P.; Raabe, G.; Bolm, C. Angew. Chem., Int. Ed. 2016, 55, 12655.
(b) Priebbenow, D. L.; Becker, P.; Bolm, C. Org. Lett. 2013, 15, 6155.
[39] Pirwerdjan, R.; Becker, P.; Bolm, C. Org. Lett. 2015, 17, 5008.
[40] (a) Kossler, D.; Perrin, F. G.; Suleymanov, A. A.; Kiefer, G.; Scopelliti, R.; Severin, K.; Cramer, N. Angew. Chem., Int. Ed. 2017, 56, 11490.
(b) Jeanbourquin, L. N.; Scopelliti, R.; Tirani, F. F.; Severin, K. Org. Lett. 2017, 19, 2070.
(c) Suleymanov, A. A.; Scopelliti, R.; Tirani, F. F.; Severin, K. Adv. Synth. Catal. 2018, 360, 4178.
(d) Tan, J. F.; Bormann, C. T.; Perrin, F. G.; Chadwick, F. M.; Seyerin, K.; Cramer, N. J. Am. Chem. Soc. 2019, 141, 10372.
[41] Perrin, F. G.; Kiefer, G.; Jeanbourquin, L.; Racine, S.; Perrotta, D.; Waser, J.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2015, 54, 13393.
[42] Landman, I. R.; Acuna-Bolomey, E.; Scopelliti, R.; Fadaei-Tirani, F.; Seyerin, K. Org. Lett. 2019, 21, 6408.
[43] Zeng, L.; Chen, R.; Zhang, C.; Xie, H.; Cui, S. Chem. Commun. 2020, 56, 3093.

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