氯磷酸二苯酯介入的芳香醛与砜缩合制备非对称芳香炔烃
收稿日期: 2017-04-30
修回日期: 2017-07-24
网络出版日期: 2017-08-16
基金资助
湖南省教育厅一般项目（No.17C0629）、湖南科技大学博士启动基金（No.E51693）、湖南科技大学理论有机化学与功能分子教育部重点实验室开放基金（No.E21630）和国家自然科学基金（No.21402048）资助项目.
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).
彭丽芬 , 蒋娟 , 彭超 , 代宁宁 , 唐子龙 , 焦银春 , 陈锦杨 , 许新华 . 氯磷酸二苯酯介入的芳香醛与砜缩合制备非对称芳香炔烃[J]. 有机化学, 2017 , 37(11) : 3013 -3018 . DOI: 10.6023/cjoc201704053
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.
[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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