研究简报

三氟甲磺酸铜(II)催化的炔丙醇快速亲核取代反应

  • 张顺吉 ,
  • 刘会丽 ,
  • 金云
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  • 淮北师范大学化学与材料科学学院 安徽淮北 235000

收稿日期: 2024-03-29

  修回日期: 2024-05-15

  网络出版日期: 2024-06-24

基金资助

安徽高校自然科学研究(2022AH050409)

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)

摘要

在三氟甲磺酸铜(II)催化下, 实现了包括吲哚、苯酚、苯甲醚、烯醇硅醚和醇在内的亲核试剂的快速炔丙基化反应, 反应条件温和, 可以在未除水溶剂中和空气条件下快速进行并获得良好的产率.

本文引用格式

张顺吉 , 刘会丽 , 金云 . 三氟甲磺酸铜(II)催化的炔丙醇快速亲核取代反应[J]. 有机化学, 2024 , 44(11) : 3531 -3540 . DOI: 10.6023/cjoc202403050

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.

参考文献

[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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