Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts
- Corresponding author: Bao Yongsheng, sbbys197812@163.com
Citation:
Menggen qiqige, Wu Yun, Bao Yongsheng. Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts[J]. Chinese Journal of Organic Chemistry,
;2018, 38(4): 902-911.
doi:
10.6023/cjoc201710034
(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.
(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.
(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.
(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.
(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.
(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.
Zhang, X. Q.; Wang, Z.-X. Org. Biomol. Chem. 2014, 12, 1448.
doi: 10.1039/c3ob41989d
(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.
Wei, W.; Zhang, C.; Xu, Y.; Wan, X. Chem. Commun. 2011, 47, 10827.
doi: 10.1039/c1cc14602e
Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem., Int. Ed. 2012, 51, 3231.
doi: 10.1002/anie.v51.13
Zhao, J.; Li, P.; Xia, C.; Li, F. Chem. Commun. 2014, 50, 4751.
doi: 10.1039/c4cc01587h
Deshidi, R.; Rizvi, M. A.; Shah, B. A. RSC Adv. 2015, 5, 90521.
doi: 10.1039/C5RA17425B
Tan, B.; Toda, N.; Barbas, C. F. Angew. Chem., Int. Ed. 2012, 51, 12538.
doi: 10.1002/anie.201205921
Huang, J.; Li, L.; Li, H.; Husan, E.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 10204.
doi: 10.1039/c2cc35450k
(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.
Kouichi, M.; Hayato, S.; Yu, M.; Kazuaki, S.; Fumi, H.; Yuki, Y.; Hirotsugu, M.; Keiji, N.; Shigenori, K. J. Oleo Sci. 2014, 63, 539.
doi: 10.5650/jos.ess13199
Kong, W.; Li, B.; Xu, X.; Song, Q. J. Org. Chem. 2016, 81, 8436.
doi: 10.1021/acs.joc.6b01594
Wang, Q.; Wang, Z.; Xu, Y.; Zhang, X.; Fan, X. Asian J. Org. Chem. 2016, 5, 1304.
doi: 10.1002/ajoc.v5.11
Nulty, J.; Nair, J. J.; Sliwinski, M.; Robertson, A. J. Tetrahedron Lett. 2009, 50, 2342.
doi: 10.1016/j.tetlet.2009.02.200
Blanc, P. Y.; Perret, A.; Teppa, F. Helv. Chim. Acta 1964, 47, 567.
doi: 10.1002/hlca.19640470224
Nishii, Y.; Akiyama, S.; Kita, Y.; Mashima, K. Synlett 2015, 26, 1831.
doi: 10.1055/s-00000083
Tahmasbi, B.; Ghorbani-Choghamarani, A. Catal. Lett. 2017, 147, 649.
doi: 10.1007/s10562-016-1927-y
Cho, C. S.; Kim, D. T.; Choi, H.; Kim, T.; Shim, S. C. Bull. Korean Chem. Soc. 2002, 23, 539.
doi: 10.5012/bkcs.2002.23.4.539
Lu, B.; Zhu, F.; Sun, H.; Shen, Q. Org. Lett. 2017, 19, 1132.
doi: 10.1021/acs.orglett.7b00148
Gaspa, S.; Porcheddu, A.; De Luca, L. Org. Lett. 2015, 17, 3666.
doi: 10.1021/acs.orglett.5b01579
Subrao, M.; Potukuchi, D. M.; Ramachandra, G.; Bhagavath, P.; Bhat, S. G.; Maddasani, S. Beilstein J. Org. Chem. 2015, 11, 233.
doi: 10.3762/bjoc.11.26
Liu, H.; Eisen, M. S. Organometallics 2017, 36, 1461.
doi: 10.1021/acs.organomet.7b00101
Beller, M.; Magerlein, W.; Indolese, A. F.; Fischer, C. Synthesis 2001, 1098.
Zhu, Z.; Yuan, J.; Zhou, Y.; Qin, Y.; Xu, J.; Peng, Y. Eur. J. Org. Chem. 2014, 2014, 511.
Bhandari, K. S.; Snieckus, V. Can. J. Chem. 1971, 49, 2354.
doi: 10.1139/v71-380
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