Sulfuric Acid Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols

  • Zhang Shunji ,
  • Liu Huili
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  • Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000

Received date: 2019-11-27

  Revised date: 2020-01-06

  Online published: 2020-01-21

Abstract

Sulfuric acid efficiently catalyzes the direct substitution of the hydroxyl group of propargylic alcohols with a variety of C- and O-based nucleophiles to aid C-C and C-O bond formation. The reactions can be performed in an undried solvent under air atmosphere to obtain the desired products in good yields. In most cases, the reaction proceeds to completion in 1 min at room temperature.

Cite this article

Zhang Shunji , Liu Huili . Sulfuric Acid Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2020 , 40(5) : 1257 -1265 . DOI: 10.6023/cjoc201911036

References

[1] (a) Zhu, H.; Ji, K.; Yang, F.; Wang, L.; Zhao, S.; Ali, S.; Liu, X.; Liang, Y. Org. Lett. 2011, 13, 684.
(b) Roy R.; Saha S. RSC Adv. 2018, 8, 31129.
(c) Zhang, X. X.; Lü, C.; Li, P.; Fu, B.; Yao, W. W. Chin. J. Org. Chem. 2016, 36, 1287(in Chinese). (张小祥, 吕昌, 李萍, 付博, 姚薇薇, 有机化学, 2016, 36, 1287.)
[2] (a) Georgy, M.; Boucard, V.; Campagne, J. J. Am. Chem. Soc. 2005, 127, 14180.
(b) Trost, B. Acc. Chem. Res. 2002, 35, 695.
(c) Georgy, M.; Boucard, V.; Campagne, J. J. Am. Chem. Soc. 2005, 127, 14180.
(d) Emer, E.; Sinisi, R.; Capdevila, M. G.; Petruzziello, D.; Vincentiis, F. D.; Cozzi, P. G. Eur. J. Org. Chem. 2011, 647.
[3] (a) Nicholas, K. M.; Mulvaney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508.
(b) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207.
(c) Berge, J.; Claridge, S.; Mann, A.; Muller, C.; Tyrrell, E. Tetrahedron Lett. 1997, 38, 685.
(d) Kuhn, O.; Rau, D.; Mayr, H. J. Am. Chem. Soc. 1998, 120, 900.
(e) Montana, A. M.; Fernandez, D. Tetrahedron Lett. 1999, 40, 6499.
(f) Teobald, B. J. Tetrahedron 2002, 58, 4133.
[4] (a) Sherry, B. D.; Radosevich, A. T.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 15760.
(b) Kennedy-Smith, J. J.; Young, L. A.; Toste, F. D. Org. Lett. 2004, 6, 1325.
(c) Ohri, R. V.; Radosevich, A. T.; Hrovat, K. J.; Musich, C.; Huang, D.; Holman, T. R. Org. Lett. 2005, 7, 2501.
[5] (a) Nishibayashi, Y.; Wakiji, I.; Hidai, M. J. Am. Chem. Soc. 2000, 122, 11019.
(b) Nishibayashi, Y.; Wakiji, I.; Ishii, Y.; Uemura, S.; Hidai, M. J. Am. Chem. Soc. 2001, 123, 3393.
(c) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 11846.
(d) Inada, Y.; Nishibayashi, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 15172.
(e) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 14, 11846.
(f) Nishibayashi, Y.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 6060.
(g) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. Angew. Chem., Int. Ed. 2003, 42, 1495.
(h) Cadierno, V.; Diez, J.; Garcia-Garrido, S. E.; Gimerno, J. Chem. Commun. 2004, 2716.
(i) Fischmeister, C.; Toupet, L.; Dixneuf, P. H. New J. Chem. 2005, 29, 765.
(j) Nishibayashi, Y.; Milton, M. D.; Inada, Y.; Yoshikawa, M.; Wakiji, I.; Hidai, M.; Uemura, S. Chem.-Eur. J. 2005, 11, 1433.
(k) Nishibayashi, Y.; Uemura, S. Curr. Org. Chem. 2006, 10, 135.
(l) Bustelo, E.; Dixneuf, P. H. Adv. Synth. Catal. 2007, 349, 933.
[6] (a) Zhan, Z.; Yang, W.; Yang, R.; Yu, J.; Li, J.; Liu, H. Chem. Commun. 2006, 3352.
(b) Jana, U.; Maiti, S.; Biswas, S. Tetrahedron Lett. 2007, 48, 7160.
(c) Yan, W.; Wang, Q.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2010, 12, 3308.
(d) Mantione, R. Bull. Soc. Chim. Fr. 1969, 4514.
(e) Hayashi, M.; Inbushi, A.; Mukaiyama, T. Bull. Soc. Chem. Jpn. 1988, 61, 4037.
(f) Shi, M.; Shouki, K.; Okamoto, Y.; Takamuku, S. J. Chem. Soc., Perkin Trans. 1 1990, 2443.
(g) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 6129.
[7] (a) Zhang, X.; Teo, W.; Chan, W. Org. Lett. 2009, 11, 4990.
(b) Gohain, M.; Marais, C.; Bezuidenhoudt, B. C. Tetrahedron Lett. 2012, 53, 1048.
[8] (a) Sanz, R.; Martínez, A.; Álvarez-Gutiérrez, J.; Rodríguez, F. Eur. J. Org. Chem. 2006, 1383.
(b) Sanz, R.; Miguel, D.; Martínez, A.; Álvarez-Gutiérrez, J.; Rodríguez, F. Org. Lett. 2007, 9, 727.
(c) Sanz, R.; Miguel, D.; Martínez, A.; Gohain, M.; García-García, P.; Fernández-Rodríguez, M.; Álvarez, E.; Rodríguez, F. Eur. J. Org. Chem. 2010, 7027.
(d) Gangadhararao, G.; Uruvakilli, A.; Kumara Swamy, K. C. Org. Lett. 2014, 16, 6060.
(e) Zhang, X.; Teng, W.; Sally, T.; Wai, P.; Chan, H. J. Org. Chem. 2010, 75, 6290.
(f) Wang T.; Chen X.; Chen L.; Zhan Z. Org. Lett. 2011, 13, 3324.
[9] Barreiro, E.; Vidal, A. S.; Tan, E.; Lau, S.; Sheppard, T. D.; González, S. D. Eur. J. Org. Chem. 2015, 7544.
[10] Savarimuthu, S. A.; Prakash, D. L.; Thomas, S. A. Tetrahedron Lett. 2014, 55, 3213.
[11] Yokosaka, T.; Shiga, N.; Nemoto, T.; Hamada, Y. J. Org. Chem. 2014, 79, 3866.
[12] Wang, L.; Xie, X.; Liu, Y. Org. Lett. 2012, 23, 5848.
[13] (a) Shaterian, H. R.; Yarahmadi, H.; Ghashang, M. Tetrahedron 2008, 64, 1263.
(b) Murugan, K.; Chen, C. Tetrahedron Lett. 2011, 52, 5827.
[14] (a) Yadav, J. S.; Reddy, B. V. S.; Reddy, A. S. J. Mol. Catal. A:Chem. 2008, 280, 219.
(b) Srihari, P.; Reddy, J. S. S.; Bhunia, D. C.; Mandal, S. S.; Yadav, J. S. Synth. Commun. 2008, 38, 1448.
(c) Srihari, P.; Reddy, J. S. S.; Mandal, S. S.; Satyanarayana, K.; Yadav, J. S. Synthesis 2008, 1853.
(d) Jang, S.; Kim, A. Y.; Seo, W. S.; Park, K. H. Nanoscale Res. Lett. 2015, 10, 2.
[15] Antonino, J. R. C.; Prez, A. L.; Corma, A. Angew. Chem., Int. Ed. 2015, 54, 5658.
[16] Yadav, J. S.; Reddy, B. V. S.; Narayanakumar, G. G. K. S.; Rao, K. V. R. Chem. Lett. 2007, 36, 942.
[17] Gujarathi, S.; Hendrickson, H. P.; Zheng, G. Tetrahedron Lett. 2013, 54, 3550.
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