Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts

doi:10.6023/cjoc201710034

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 902-911.DOI: 10.6023/cjoc201710034 Previous Articles Next Articles

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季铵盐与醛或羧酸的无金属酯化反应研究

孟根其其格, 乌云, 包永胜

内蒙古师范大学化学与环境科学学院内蒙古绿色催化重点实验室呼和浩特 010022

收稿日期:2017-10-26 修回日期:2017-11-26 发布日期:2017-12-05
通讯作者: 包永胜 E-mail:sbbys197812@163.com
基金资助:
国家自然科学基金（No.21462031）、内蒙古自治区高等学校青年科技英才支持计划（No.NJYT-17-A22）资助项目.

Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts

Menggen qiqige, Wu Yun, Bao Yongsheng

College of Chemistry and Environmental Science, Inner Mongolia Key Laboratory of Green Catalysis, Inner Mongolia Normal University, Hohhot 010022

Received:2017-10-26 Revised:2017-11-26 Published:2017-12-05
Contact: 10.6023/cjoc201710034 E-mail:sbbys197812@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21462031) and the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region (No. NJYT-17-A22).

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Menggen qiqige, Wu Yun, Bao Yongsheng. Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts[J]. Chin. J. Org. Chem., 2018, 38(4): 902-911.

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[1] (a) Cassar, L.; Foa, M.; Gardano, A. J. Organomet. Chem. 1976, 121, C55.
(b) Bhardwaj, M.; Sahi, S.; Mahajan, H.; Paul, S.; Clark, J. H. J. Mol. Catal. A:Chem. 2015, 408, 48.
(c) Zhang, J. T.; Li, D. Y.; Chen, H.; Wang, B. J.; Liu, Z. X.; Zhang, Y. H. Adv. Synth. Catal. 2016, 358, 792.
[2] (a) Wang, X.; Zhu, L. Z.; Chen, S. H.; Xu, X. H.; Au, C. T.; Qiu, R. Org. Lett. 2015, 17, 5228.
(b) Lin, C. L.; Li, D.; Wang, Y. B.; Yao, J. Z.; Zhang, Y. H. Org. Lett. 2015, 17, 1328.
(c) Fabrizi, G.; Goggiamani, A.; Sferrazza, A.; Cacchi, S. Angew. Chem., Int. Ed. 2010, 49, 4067.
(d) Thirupathi, N.; Puri, S.; Reddy, T. J.; Sridhar, B.; Reddya, M. S. Adv. Synth. Catal. 2016, 358, 303.
(e) Xu, P.; Han, F. S.; Wang, Y. H. Adv. Synth. Catal. 2015, 357, 3441.
(f) Gadge, S. T.; Khedkar, M. V.; Lanke, S. R.; Bhanage, B. M. Adv. Synth. Catal. 2012, 354, 2049.
[3] (a) Hirao, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. J. Organomet. Chem. 1982, 236, 409.
(b) Hosomi, A.; Hoashi, K.; Kohra, S.; Tominaga, Y.; Otaka, K.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1987, 570.
(c) Bao, H.; Qi, X.; Tambar, U. K. J. Am. Chem. Soc. 2011, 133, 1206.
[4] (a) Wenkert, E.; Han, A.-L.; Jenny, C.-J. J. Chem. Soc., Chem. Commun. 1988, 975.
(b) Reeves, J. T.; Fandrick, D. R.; Tan, Z.; Song, J. J.; Lee, H.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2010, 12, 4388.
(c) Guo, W.-J.; Wang, Z.-X. Tetrahedron 2013, 69, 9580.
[5] (a) Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
(b) Maity, P.; Shacklady-McAtee, D. M.; Yap, G. P. A.; Sirianni, E. R.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 280.
[6] (a) Xie, L.-G.; Wang, Z.-X. Angew. Chem., Int. Ed. 2011, 50, 4901.
(b) Zhang, X.-Q.; Wang, Z.-X. J. Org. Chem. 2012, 77, 3658.
[7] Zhang, X. Q.; Wang, Z.-X. Org. Biomol. Chem. 2014, 12, 1448.
[8] (a) Uyanik, M.; Ishihara, K. ChemCatChem 2012, 4, 177.
(b) Xue, Q. C.; Xie, J.; Li, H. M.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2013, 49, 3700.
(c) Zhao, D.; Wang, T.; Shen, Q.; Li, J. X. Chem. Commun. 2014, 50, 4302.
(d) Wei, W.; Zhang, C.; Xu, Y.; Wan, X. B. Chem. Commun. 2011, 47, 10827.
(e) Liu, L. H.; Yun, L.; Wang, Z. K.; Fu, X. F.; Yan, C. H. Tetrahedron Lett. 2013, 54, 5383.
(f) Li, D. J.; Yang, T. H.; Su, H. L.; Yu, W. Adv. Synth. Catal. 2015, 357, 2529.
(g) Hao, W. J.; Du, Y.; Wang, D.; Jiang, B.; Gao, Q.; Tu, S. J.; Li, G. G. Org. Lett. 2016, 18, 1884.
(h) Zhang, H.; Dong, D. Q.; Hao, S. H.; Wang, Z. L. RSC Adv. 2016, 6, 8465.
(i) Sun, J. W.; Wang, Y.; Pan, Y. J. Org. Chem. 2015, 80, 8945.
(j) Uyanik, M.; Okamoto, H.; Yasui, T.; Ishihara, K. Science 2010, 328, 1376.
(k) Kim, H. J.; Kim, J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382.
(l) Rao, H.; Ma, X.; Liu, Q.; Li, Z.; Cao, S.; Li, C.-J. Adv. Synth. Catal. 2013, 355, 2191.
[9] Wei, W.; Zhang, C.; Xu, Y.; Wan, X. Chem. Commun. 2011, 47, 10827.
[10] Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem., Int. Ed. 2012, 51, 3231.
[11] Zhao, J.; Li, P.; Xia, C.; Li, F. Chem. Commun. 2014, 50, 4751.
[12] Deshidi, R.; Rizvi, M. A.; Shah, B. A. RSC Adv. 2015, 5, 90521.
[13] Tan, B.; Toda, N.; Barbas, C. F. Angew. Chem., Int. Ed. 2012, 51, 12538.
[14] Huang, J.; Li, L.; Li, H.; Husan, E.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 10204.
[15] (a) Fox, S. C.; Li, B.; Xu, D.; Edgar, K. J. Biomacromolecules 2011, 12, 1956.
(b) Otera, J.; Nishikido, J. Esterification, Methods, Reactions, and Applications, 2nd ed., Wiley-VCH, Weinheim, 2010.
(c) Otera, J. Chem. Rev. 1993, 93, 1449.
(d) Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551.
[16] Kouichi, M.; Hayato, S.; Yu, M.; Kazuaki, S.; Fumi, H.; Yuki, Y.; Hirotsugu, M.; Keiji, N.; Shigenori, K. J. Oleo Sci. 2014, 63, 539.
[17] Kong, W.; Li, B.; Xu, X.; Song, Q. J. Org. Chem. 2016, 81, 8436.
[18] Wang, Q.; Wang, Z.; Xu, Y.; Zhang, X.; Fan, X. Asian J. Org. Chem. 2016, 5, 1304.
[19] Nulty, J.; Nair, J. J.; Sliwinski, M.; Robertson, A. J. Tetrahedron Lett. 2009, 50, 2342.
[20] Blanc, P. Y.; Perret, A.; Teppa, F. Helv. Chim. Acta 1964, 47, 567.
[21] Nishii, Y.; Akiyama, S.; Kita, Y.; Mashima, K. Synlett 2015, 26, 1831.
[22] Tahmasbi, B.; Ghorbani-Choghamarani, A. Catal. Lett. 2017, 147, 649.
[23] Cho, C. S.; Kim, D. T.; Choi, H.; Kim, T.; Shim, S. C. Bull. Korean Chem. Soc. 2002, 23, 539.
[24] Lu, B.; Zhu, F.; Sun, H.; Shen, Q. Org. Lett. 2017, 19, 1132.
[25] Gaspa, S.; Porcheddu, A.; De Luca, L. Org. Lett. 2015, 17, 3666.
[26] Subrao, M.; Potukuchi, D. M.; Ramachandra, G.; Bhagavath, P.; Bhat, S. G.; Maddasani, S. Beilstein J. Org. Chem. 2015, 11, 233.
[27] Liu, H.; Eisen, M. S. Organometallics 2017, 36, 1461.
[28] Beller, M.; Magerlein, W.; Indolese, A. F.; Fischer, C. Synthesis 2001, 1098.
[29] Zhu, Z.; Yuan, J.; Zhou, Y.; Qin, Y.; Xu, J.; Peng, Y. Eur. J. Org. Chem. 2014, 2014, 511.
[30] Bhandari, K. S.; Snieckus, V. Can. J. Chem. 1971, 49, 2354.

季铵盐与醛或羧酸的无金属酯化反应研究

Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts

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