NOTE

Cu(OTf)2 Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols

  • Shunji Zhang ,
  • Huili Liu ,
  • Yun Jin
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  • College of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000
*Corresponding author. E-mail:

Received date: 2024-03-29

  Revised date: 2024-05-15

  Online published: 2024-06-24

Supported by

Natural Science Research Project of Anhui Educational Committee(2022AH050409)

Abstract

The propargylation of various nucleophiles including indoles, phenol, anisole, enoxysilanes, and alcohols was rapidly achieved using catalytic copper(II) triflate. The reaction conditions are mild, allowing for quick reactions in an undried solvent and under atmospheric air. The desired products are obtained with good yields.

Cite this article

Shunji Zhang , Huili Liu , Yun Jin . Cu(OTf)2 Catalyzed Rapid Nucleophilic Substitution of Propargyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2024 , 44(11) : 3531 -3540 . DOI: 10.6023/cjoc202403050

References

[1]
(a) Zou F.; Luo Z.; Yang Y.; Zhuang X.; Hong C.; Liu Z.; Li W.; Li Q.; Liu T. J. Org. Chem. 2022, 87, 15061.
[1]
(b) Goswami J.; Haque N.; Seikh A.; Bhattacharya B.; Emmerling F.; Bar N.; Ifseisi A.; Biswas S.; Dolai M. J. Mol. Struct. 2024, 136868.
[1]
(c) Kitamura M.; Nishimura T.; Otsuka K.; Hirokazu Shimooka H.; Okauchi T. Tetrahedron Lett. 2020, 61, 151853.
[1]
(d) Luo F.; He S.; Gou Q.; Chen J.; Zhang M. Tetrahedron Lett. 2021, 64, 152724.
[1]
(e) Zhang X. X.; Lv C.; Li P.; Fu B.; Yao W. Chin. J. Org. Chem. 2016, 36, 1287 (in Chinese).
[1]
(张小祥, 吕昌, 李萍, 付博, 姚薇薇, 有机化学, 2016, 36, 1287.)
[2]
(a) Trost B.; Crawley M. Chem. Rev. 2003, 103, 2921.
[2]
(b) Ma S.; Yu S.; Peng Z.; Guo H. J. Org. Chem. 2006, 71, 9865.
[2]
(c) Yadav J. S.; Reddy B. V. S.; Basak A. K.; Narsaiah A. V.; Prabhakar A.; Jagadeesh B. Tetrahedron Lett. 2005, 46, 639.
[3]
(a) Westermaier M.; Mayr H. Org. Lett. 2006, 8, 4791.
[3]
(b) Bandini M.; Melloni A.; Umani-Ronchi A. Org. Lett. 2004, 6, 3199.
[3]
(c) De la Herrán G.; Segura A.; Csáky A. G. Org. Lett. 2007, 9, 961.
[3]
(d) Liu Z.; Liu L.; Shafiq Z.; Wu Y. C.; Wang D.; Chen Y. J. Tetrahedron Lett. 2007, 48, 3963.
[4]
(a) Georgy M.; Boucard V.; Campagne J. J. Am. Chem. Soc. 2005, 127, 14180.
[4]
(b) Trost B. Acc. Chem. Res. 2002, 35, 695.
[4]
(c) Emer E.; Sinisi R.; Capdevila M. G.; Petruzziello D.; Vincentiis F. D.; Cozzi P. G. Eur. J. Org. Chem. 2011, 647.
[5]
(a) Nicholas K. M. Acc. Chem. Res. 1987, 20, 207.
[5]
(b) Kuhn O.; Rau D.; Mayr H. J. Am. Chem. Soc. 1998, 120, 900.
[5]
(c) Montana A. M.; Fernandez D. Tetrahedron Lett. 1999, 40, 6499.
[5]
(d) Teobald B. J. Tetrahedron 2002, 58, 4133.
[6]
(a) Sherry B. D.; Radosevich A. T.; Toste F. D. J. Am. Chem. Soc. 2003, 125, 15760.
[6]
(b) Kennedy-Smith J. J.; Young L. A.; Toste F. D. Org. Lett. 2004, 6, 1325.
[6]
(c) Ohri R. V.; Radosevich A. T.; Hrovat K. J.; Musich C.; Huang D.; Holman T. R. Org. Lett. 2005, 7, 2501.
[7]
(a) Nishibayashi Y.; Milton M. D.; Inada Y.; Yoshikawa M.; Wakiji I.; Hidai M.; Uemura S. Chem.-Eur. J. 2005, 11, 1433.
[7]
(b) Bustelo E.; Dixneuf P. H. Adv. Synth. Catal. 2007, 349, 933.
[8]
(a) Zhan Z.; Yang W.; Yang R.; Yu J.; Li J.; Liu H. Chem. Commun. 2006, 3352.
[8]
(b) Jana U.; Maiti S.; Biswas S. Tetrahedron Lett. 2007, 48, 7160.
[8]
(c) Yan W.; Wang Q.; Chen Y.; Petersen J. L.; Shi X. Org. Lett. 2010, 12, 3308.
[9]
(a) Sanz R.; Martínez A.; álvarez-Gutiérrez J.; Rodríguez F. Eur. J. Org. Chem. 2006, 1383.
[9]
(b) Sanz R.; Miguel D.; Martínez A.; álvarez-Gutiérrez J.; Rodríguez F. Org. Lett. 2007, 9, 727.
[9]
(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.
[9]
(d) Rao G.; Uruvakilli A.; Kumara Swamy K. C. Org. Lett. 2014, 16, 6060.
[9]
(e) Zhang X.; Teng W.; Sally T.; Wai P.; Chan H. J. Org. Chem. 2010, 75, 6290.
[9]
(f) Wang T.; Chen X.; Chen L.; Zhan Z. Org. Lett. 2011, 13, 3324.
[10]
Barreiro E.; Vidal A. S.; Tan E.; Lau S.; Sheppard T.; González S. Eur. J. Org. Chem. 2015, 7544.
[11]
Savarimuthu S. A.; Prakash D. L.; Thomas S. A. Tetrahedron Lett. 2014, 55, 3213.
[12]
Yokosaka T.; Shiga N.; Nemoto T.; Hamada Y. J. Org. Chem. 2014, 79, 3866.
[13]
Mothe S.; Chan P. J. Org. Chem. 2009, 74, 5887.
[14]
Murugan K.; Chen C. Tetrahedron Lett. 2011, 52, 5827.
[15]
Srihari P.; Reddy J.; Bhunia D.; Mandal S.; Yadav J. Synth. Commun. 2008, 38, 1448.
[16]
Antonino J.; Prez A.; Corma A. Angew. Chem., Int. Ed. 2015, 54, 5658.
[17]
Yadav J.; Reddy B.; Narayanakumar G.; Rao K. Chem. Lett. 2007, 36, 942.
[18]
Gujarathi S.; Hendrickson H. P.; Zheng G. Tetrahedron Lett. 2013, 54, 3550.
[19]
Zhang X.; Teo W.; Chan W. Org. Lett. 2009, 11, 4990.
[20]
Silveira C.; Mendes S.; Martins G. Tetrahedron Lett. 2012, 53, 1567.
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