Chinese Journal of Organic Chemistry >
Synthesis of Unsymmetrical Aromatic Acetylenes by Diphenyl Chlorophosphate-Promoted Condensation Reaction of Aromatic Aldehydes and Sulfones
Received date: 2017-04-30
Revised date: 2017-07-24
Online published: 2017-08-16
Supported by
Project supported by the General Project of Hunan Education Department (No. 17C0629), the Doctoral Foundation of Hunan University of Science and Technology (No. E51693), the Open Foundation of Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology (No. E21630), the National Natural Science Foundation of China (No. 21402048).
Diphenyl chlorophosphate-promoted condensation reaction of aromatic aldehydes and sulfones, proceeding at room temperature, could been applied to synthesize unsymmetrical aromatic acetylenes. It was found that functional groups on aromatic ring of aldehydes and sulfones had little effect on the reaction. A series of unsymmetrical diphenyl, thienyl, pyridyl, coumarin and diphenylphosphoryl aromatic acetylenes were prepared by the reaction. Based on the molecular structure, the reason why this reaction could proceed at room temperature is explained The reaction showed some outstanding features including simple operation, wide functional group tolerance, high yields and mild reaction conditions.
Peng Lifen , Jiang Juan , Peng Chao , Dai Ningning , Tang Zilong , Jiao Yinchun , Chen Jinyang , Xu Xinhua . Synthesis of Unsymmetrical Aromatic Acetylenes by Diphenyl Chlorophosphate-Promoted Condensation Reaction of Aromatic Aldehydes and Sulfones[J]. Chinese Journal of Organic Chemistry, 2017 , 37(11) : 3013 -3018 . DOI: 10.6023/cjoc201704053
[1] Lu, W.; Haji, G. Z.; Aisa, A.; Cai, J. Tetrahedron Lett. 1998, 39, 9521.
[2] Zhao, X.-G.; Ma, L.-C.; Zhang, L.; Wen, Y.-G.; Chen, J.-M.; Shuai, Z.-G.; Liu, Y.-Q.; Zhan, X.-W. Macromolecules 2013, 46, 2152.
[3] Justin Thomas, K. R.; Kapoor, N.; Prasad Bolisetty, M. N. K.; Jou, J.-H.; Chen, Y.-L.; Jou, Y.-C. J. Org. Chem. 2012, 77, 3921.
[4] Matsuo, D.; Yang, X.; Hamada, A.; Morimoto, K.; Kato, T.; Yahiro, M.; Adachi, C.; Orita, A.; Otera, J. Chem. Lett. 2010, 39, 1300.
[5] Yao, Z-Y.; Zhang, M.; Wu, H.; Yang, L.; Li, R-Z.; Wang, P. J. Am. Chem. Soc. 2015, 137, 3799.
[6] Fischer, M.; Lieser, G.; Rapp, A.; Schnell, I.; Mamdouh, W.; Feyter, S. D.; Schryver, F. C.; Höger, S. J. Am. Chem. Soc. 2004, 126, 214.
[7] He, Z.-H.; Lai, G.-Q.; Li, Z.-F.; Yuan, X.; Shen, Y.-J.; Wang, C.-Y. Chin. J. Chem. 2015, 33, 550.
[8] Peng, L.-F.; Xu, F.; Suzuma, Y.; Orita, A.; Otera, J. J. Org. Chem. 2013, 78, 12802.
[9] Yang, X.; Matsuo, D.; Suzuma, Y.; Fang, J.-K.; Xu, F.; Orita, A.; Otera, J.; Kajiyama, S.; Koumura, N.; Hara, K. Synlett 2011, 2402.
[10] Orita, A.; Hasegawa, D.; Nakano, T.; Otera, J. Chem.-Eur. J. 2002, 8, 2000.
[11] Guan, Z. P.; Shi, Y.;Shi, W.; Chen, H. Chin. J. Org. Chem. 2017, 37, 418(in Chinese). (关志朋, 师瑶, 石炜, 陈浩, 有机化学, 2017, 37, 418.)
[12] Wang, M. M.; Wang, Z. X.; Shang, M.; Dai, H. X. Chin. J. Org. Chem. 2015, 35, 570(in Chinese). (王明明, 王子潇, 商明, 戴辉雄, 有机化学, 2015, 35, 570.)
[13] Orita, A.; Otera, J. Chem. Rev. 2006, 106, 5387.
[14] (a) Orita, A.; Yoshioka, N.; Struwe, P.; Braier, A.; Beckmann, A.; Otera, J. Chem.-Eur. J. 1999, 5, 1355.
(b) Orita, A.; Miyamoto, K.; Nakashima, M.; Ye, F.-G.; Otera, J. Adv. Synth. Catal. 2004, 346, 767.
[15] Orita, A.; Taniguchi, H.; Otera, J. Chem. Asian J. 2006, 1, 430.
[16] Peng, L.-F.; Xu, F.; Shinohara, K.; Orita, A.; Otera, J. Org. Chem. Front. 2015, 2, 248.
[17] Peng, L.-F.; Xu, F.; Shinohara, K.; Orita, A.; Otera, J. Chem. Lett. 2014, 43, 1610.
[18] Iyengar, R. R.; Lynch, J. K.; Mulhern, M. M.; Judd, A. S.; Freeman, J. C.; Gao, J.; Souers, A. J.; Zhao, G.; Wodka, D.; Doug F., H.; Brodjian, S.; Dayton, B. D.; Reilly, R. M.; Swanson, S.; Su, Z.; Martin, R. L.; Leitza, S. T.; Houseman, K. A.; Diaz, G.; Collins, C. A.; Sham, H. L.; Kym, P. R. Bioorg. Med. Chem. Lett. 2007, 17, 874.
[19] Jin, M.-J.; Lee, D.-H. Angew. Chem., Int. Ed. 2010, 49, 1119.
[20] Li, X.; Yang, F.; Wu, Y.-J. J. Org. Chem. 2013, 78, 4543.
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