Synthesis of Unsymmetrical Aromatic Acetylenes by Diphenyl Chlorophosphate-Promoted Condensation Reaction of Aromatic Aldehydes and Sulfones

doi:10.6023/cjoc201704053

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 3013-3018.DOI: 10.6023/cjoc201704053 Previous Articles Next Articles

Notes

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

彭丽芬^a, 蒋娟^a, 彭超^a, 代宁宁^a, 唐子龙^a, 焦银春^a, 陈锦杨^b, 许新华^b

a 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精细聚合物可控制备及功能化应用湖南省重点实验室湖南科技大学化学化工学院湘潭 411201;
b 湖南大学化学化工学院化学生物传感与计量学国家重点实验室长沙 410082

收稿日期:2017-04-30 修回日期:2017-07-24 发布日期:2017-08-16
通讯作者: 彭丽芬, 许新华 E-mail:1060137@hnust.edu.cn;xhx1581@hnu.edu.cn
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

Peng Lifen^a, Jiang Juan^a, Peng Chao^a, Dai Ningning^a, Tang Zilong^a, Jiao Yinchun^a, Chen Jinyang^b, Xu Xinhua^b

a Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201;
b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2017-04-30 Revised:2017-07-24 Published:2017-08-16
Contact: 10.6023/cjoc201704053 E-mail:1060137@hnust.edu.cn;xhx1581@hnu.edu.cn
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).

1. Synthesis of Unsymmetrical Aromatic Acetylenes by Diphenyl Chlorophosphate-Promoted Condensation Reaction of Aromatic Aldehydes and Sulfones.PDF(3806KB)

Abstract

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.

Key words: condensation reaction, unsymmetrical aromatic acetylene, coumarin acetylene, diphenylphosphoryl aromatic acetylene

Cite this article

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]. Chin. J. Org. Chem., 2017, 37(11): 3013-3018.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

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

Synthesis of Unsymmetrical Aromatic Acetylenes by Diphenyl Chlorophosphate-Promoted Condensation Reaction of Aromatic Aldehydes and Sulfones

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	JIan Xiao, Zhiying Wu, Ziyi Chen, Pengfei Zhao. Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1179-1187.
[2]	Wang Lingfeng, Qian Ying. Near-Infrared Quinoline-Fluoroborodipyrrole Dye: Synthesis and Lysosomal Fluorescence Imaging [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1246-1250.
[3]	Wei Li, Chen Xuwen, Liu Yunyun, Wan Jieping. Recent Advances in Organic Synthesis Employing Ethyl Lactate as Green Reaction Medium [J]. Chin. J. Org. Chem., 2016, 36(5): 954-961.
[4]	Xu Zhaohui, Zhou Peng, Liu Deyong. Efficient One-Pot Synthesis of 3,3-Dimethyl-diphenyl-2,4-dioxa-8,10-diazaspiro[5.5]undecane-1,5-dione-9-thione Derivatives [J]. Chin. J. Org. Chem., 2016, 36(5): 1099-1103.
[5]	Xu Zhaohui, Tu Yuanhong. Solvent-Free Synthesis of Spiro Heterobicyclic Derivatives under Ultrasonic Irradiation with Dawson-Type Tungsten Vanado Phosphoric Heteropoly Acid as Catalyst [J]. Chin. J. Org. Chem., 2015, 35(6): 1357-1362.
[6]	Chen Jinfang, Xu Xiaoliang, Li Xiaonian. Research Development on the Condensation Reaction of Conjugated Olefine Acid and Polyethylene Glycol [J]. Chin. J. Org. Chem., 2015, 35(1): 39-54.
[7]	Wang Wenli, He Qing, Ding Ru, He Yun, Zhang Zunting. Synthesis of 1-Hydroxy-2-phenyltriphenylene Derivatives by Three-Step Condensation [J]. Chin. J. Org. Chem., 2014, 34(9): 1875-1880.
[8]	Xu Zhaohui. Solvent-Free Synthesis of 5-[(Indol-3-yl)-methyl]-2,2-dimethyl-1,3- dioxane-4,6-dione Derivatives under Ultrasonic Irradiation with Succinimide-N-sulfonic Acid Cerium as Catalyst [J]. Chin. J. Org. Chem., 2014, 34(8): 1687-1691.
[9]	Li Zhongxian, Wang Junwei, Zhao Junhong, Zhao Canfang, Liu Xiaopei, Yu Xuejun. Advanced in the Synthesis of Triarylmethanes [J]. Chin. J. Org. Chem., 2014, 34(3): 485-494.
[10]	Xu Zhaohui, Lin Chunhua. Solvent-Free Synthesis of 5-Alkenyl-2,2-pentamethylene-1,3-dioxane-4,6-diones under Ultrasonic Irradiation with CePW₁₂O₄₀ as Catalyst [J]. Chin. J. Org. Chem., 2013, 33(07): 1540-1544.
[11]	WANG Hong-She, ZENG Jun-E. Mg(NTf) Catalyzed Efficient Synthesis of Quinoline Derivatives via Friedl?nder Condensation Reaction [J]. Chin. J. Org. Chem., 2010, 30(07): 1072-1075.
[12]	Quan, Zhengjun ; Zhang, Zhang; Da, Yuxia; Wang, Xicun*. New Advances in the Synthesis of Biginelli 3,4-Dihydropyrimidin-2(1H)-one Derivatives [J]. Chin. J. Org. Chem., 2009, 29(06): 876-883.
[13]	Yuan, Sichun*; Wang, Huichuan ; Chen, Haibo. Advances in the Synthesis of Terpyridine Ligand and Its Derivatives [J]. Chin. J. Org. Chem., 2009, 29(04): 504-516.
[14]	. Progress in Catalyst Systems for the Friedländer Reaction [J]. Chin. J. Org. Chem., 2009, 29(01): 1-12.
[15]	ZHANG Ying-Qun*, MA Jing-Jun, WANG Chun, LI Jing-Ci ZHANG Dong-Nuan, ZANG Xiao-Huan, LI Jie. One-Pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones [J]. Chin. J. Org. Chem., 2008, 28(01): 141-144.