膦酰保护基促进选择性Hay偶联制备非对称1,3-二炔

doi:10.6023/cjoc201805009

有机化学 ›› 2018, Vol. 38 ›› Issue (11): 3048-3055.DOI: 10.6023/cjoc201805009 上一篇下一篇

所属专题：元素有机化学合辑2018-2019

研究论文

膦酰保护基促进选择性Hay偶联制备非对称1,3-二炔

彭丽芬^a, 彭超^a, 汪明^a, 唐子龙^a, 焦银春^a, 许新华^b

a 湖南科技大学化学化工学院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:2018-05-02 修回日期:2018-05-30 发布日期:2018-07-05
通讯作者: 彭丽芬, 唐子龙 E-mail:1060137@hnust.edu.cn;zltang@hnust.edu.cn
基金资助:
国家自然科学基金（No.21402048）、湖南省自然科学基金（No.2018JJ3145）、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）资助项目.

Phosphoryl Protecting Group Enabled Facile Synthesis of Unsymmetrical 1,3-Diynes by Selective Hay Coupling

Peng Lifen^a, Peng Chao^a, Wang Ming^a, Tang Zilong^a, Jiao Yinchun^a, 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:2018-05-02 Revised:2018-05-30 Published:2018-07-05
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21402048), the Natural Science Fund Youth Project of Hunan Province (No. 2018JJ3145), the General Project of Hunan Education Department (No. 17C0629) and the Doctoral Foundation of Hunan University of Science and Technology (No. E51693).

文章分享

1. 膦酰保护基促进选择性Hay偶联制备非对称1,3-二炔.PDF(57674KB)

摘要/Abstract

报道了芳香末端炔烃与单膦酰基-保护二炔的选择性Hay偶联反应.Ph₂P（O）的极性使得产物非对称1，3-二炔易与副产物分离.单膦酰基-保护二炔的低反应活性减少了自身氧化偶联，从而提高了目标产物的产率.很多芳香末端炔烃与单膦酰基-保护二炔都能应用于本Hay偶联反应，且相应非对称1，3-二炔产物的产率为中等到好.产物非对称1，3-二炔能用于合成非对称炔-二炔烃及环多炔烃.

关键词: Hay偶联, 非对称1,3-二炔, 末端炔烃, 膦酰保护基

A selective Hay coupling reaction of aromatic terminal acetylenes and monophosphoryl-protected diynes was developed. The polarity of Ph₂P(O) realized facile isolation of the desired unsymmetrical 1,3-diynes from by-products. The low reactivity of monophosphoryl-protected diynes reduced the oxidative homocoupling of itself and enhanced the yields of desired products. A number of aromatic terminal acetylenes and monophosphoryl-protected diynes were tolerated in this reaction, and all the corresponding unsymmetrical 1,3-diynes could be obtained in moderate to good yields. The unsymmetrical 1,3-diynes could be applied to synthesize unsymmetrical yne-diynes and cyclic polyynes.

Key words: Hay coupling, unsymmetrical 1,3-diyne, terminal acetylene, phosphoryl protecting group

引用此文

彭丽芬, 彭超, 汪明, 唐子龙, 焦银春, 许新华. 膦酰保护基促进选择性Hay偶联制备非对称1,3-二炔[J]. 有机化学, 2018, 38(11): 3048-3055.

Peng Lifen, Peng Chao, Wang Ming, Tang Zilong, Jiao Yinchun, Xu Xinhua. Phosphoryl Protecting Group Enabled Facile Synthesis of Unsymmetrical 1,3-Diynes by Selective Hay Coupling[J]. Chin. J. Org. Chem., 2018, 38(11): 3048-3055.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Stang, P. J.; Diederich, F. Modern Acetylene Chemistry, VCH, Weinheim, 1995.
[2] Shi, W.; Lei, A.-W. Tetrahedron Lett. 2014, 55, 2763.
[3] (a) Ito, A.; Cui, B.; Chavez, D.; Chai, H. B.; Shin,Y. G.; Kawanishi, K.; Kardono, L. B.; Riswan, S.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 2001, 64, 246.
(b) Evano, G.; Blanchard, N. Copper-Mediated Cross-Coupling Reactions, John Wiley & Sons, Inc., Hoboken, NJ, 2014.
(c) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2632.
[4] Guo, L.; Song, L.; Wang, Z.; Zhao, W.; Mao, W.; Yin, M. Chem. Biol. Interact. 2009, 181, 138.
[5] (a) Katano, M.; Yamamoto, H.; Matsunaga, H.; Mori, M.; Takata, K.; Nakamura, M. Gan to Kagaku Ryoho 1990, 17, 1045.
(b) Matsunaga, H.; Saita, T.; Naguo, F.; Mori, M.; Katano, M. Cancer Chemother. Pharmacol. 1995, 35, 291.
[6] (a) Yadav, J. S.; Kumaraswamy, B.; Sathish Reddy, A.; Srihari, P.; Janakiram, R. V.; Kalivendi, S. V. J. Org. Chem. 2011, 76, 2568.
(b) Srihari, P.; Sathish Reddy, A.; Deepthi, Y.; Kalivendi, S. Tetrahedron Lett. 2013, 54, 5616.
[7] Gangadhar, P.; Reddy, S. A.; Srihari, P. Tetrahedron 2016, 72, 5807.
[8] (a) Fang, J.-K.; Sun, T.-X.; Tian, Y.; Zhang, Y.-J.; Jin, C.-F.; Xu, Z.-M.; Hu, X.-Y.; Wang, H.-B. Mater. Chem. Phys. 2017, 195, 1.
(b) Peng, L.-F.; Wang, B.-H.; Wang, M.; Tang, Z.-L.; Jiang, Y.-Z.; Jiao, Y.-C.; Xu, X.-H. J. Chem. Res. 2018, 42, 235.
(c) Peng, L.-F.; Lei, J.-Y.; Wu, L.; Tang, Z.-L.; Luo, Z.-P.; Jiao, Y.-C.; Xu, X.-H. J. Chem. Res. 2018, 42, 271.
[9] Pati, A. K.; Mohapatra, M.; Ghosh, P.; Gharpure, S. J.; Mishra, A. K. J. Phys. Chem. A 2013, 117, 6548.
[10] (a) Wan,W. B.; Brand, S. C.; Pak, J. J.; Haley, M. M. Chem.-Eur. J. 2005, 6, 2044.
(b) Peng, L.-F.; Jiang, J.; Peng, C.; Dai, N.-N.; Tang, Z.-L.; Jiao, Y.-C.; Chen, J.-Y.; Xu, X.-H. Chin. J. Org. Chem. 2017, 37, 3013(in Chinese). (彭丽芬, 蒋娟, 彭超, 代宁宁, 唐子龙, 焦银春, 陈锦杨, 许新华, 有机化学, 2017, 37, 3013.)
(c) Peng, L.-F.; Zhang, S.-W.; Wang, B.-H.; Xun, M.-S.; Tang, Z.-L.; Jiao, Y.-C.; Xu, X.-H. Chin. J. Org. Chem. 2018, 38, 519(in Chinese). (彭丽芬, 张思维, 王丙昊, 寻梦硕, 唐子龙, 焦银春, 许新华, 有机化学, 2018, 38, 519.)
[11] (a) Li, Y.-N.; Wang, J.-L.; He, L.-N. Tetrahedron Lett. 2011, 52, 3485.
(b) Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Gayathri, K. U.; Prasad, A. R. Tetrahedron Lett. 2003, 44, 6493.
[12] (a) Hay, A. J. Org. Chem. 1960, 25, 1275.
(b) Abe, H.; Kurokawa, H.; Chida, Y.; Inouye, M. J. Org. Chem. 2011, 76, 309.
[13] (a) Hay, A. S. J. Org. Chem. 1962, 27, 3320.
(b) Montierth, J. M.; DeMario, D. R.; Kurth, M. J.; Schore, N. E. Tetrahedron 1998, 54, 11741.
[14] (a) Bandyopadhyay, A.; Varghese, B.; Sankararaman, S. J. Org. Chem. 2006, 71, 4544.
(b) Cahiez, G.; Moyeux, A. Chem. Rev. 2010, 110, 1435.
[15] (a) Allen, S. E.; Walvoord, R. R.; Padilla-Salinas, R.; Kozlowski, M. C. Chem. Rev. 2013, 113, 6234.
(b) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
(c) Stefani, H. A.; Guarezemini, A. S.; Cella, R. Tetrahedron 2010, 66, 7871.
(d) Jia, X.; Yin, K.; Li, C.; Li, J.; Bian, H. Green Chem. 2011, 13, 2175.
(e) Kamata, K.; Yamaguchi, S.; Kotani, M.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2008, 47, 2407.
(f) Crowley, J. D.; Goldup, S. M.; Gowans, N. D.; Leigh, D. A.; Ronaldson, V. E.; Slawin, A. M. Z. J. Am. Chem. Soc. 2010, 132, 6243.
(g) Gao, H.-Y.; Wagner, H.; Zhong, D.; Franke, J.-H.; Studer, A.; Fuchs, H. Angew. Chem., Int. Ed. 2013, 52, 4024.
(h) Zhang, S.; Liu, X.; Wang, T. Adv. Synth. Catal. 2011, 353, 1463.
(i) Balamurugan, R.; Naveen, N.; Manojveer, S.; Nama, M. V. Aust. J. Chem. 2011, 64, 567.
(j) Wong, W.-Y.; Lu, G.-L.; Choi, K.-H.; Guo, Y.-H. J. Organomet. Chem. 2005, 690, 177.
(k) Navale, B. S.; Bhat, R. G. RSC Adv. 2013, 3, 5220.
(l) Liu, Y.; Wang, C.; Wang, X.; Wan, J.-P. Tetrahedron Lett. 2013, 54, 3953.
[16] (a) Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2009, 11, 709.
(b) Suarez, J. R.; Collado-Sanz, D.; Cardenas, D. J.; Chiara, J. L. J. Org. Chem. 2015, 80, 1098.
(c) Balaraman, K.; Kesavan, V. Synthesis 2010, 3461.
(d) Lampkowski, J. S.; Durham, C. E.; Padilla, M. S.; Young, D. D. Org. Biomol. Chem. 2015, 13, 424.
[17] (a) Cadiot, P.; Chodkiewicz, W. Chemistry of Acetylenes, Marcel Dekker, New York, 1969.
(b) Sindhu, K. S.; Thankachan, A. P.; Sajitha, P. S.; Anilkumar, G. Org. Biomol. Chem. 2015, 13, 6891.
(c) Yu, M.; Pan, D.; Jia, W.; Chen, W.; Jiao, N. Tetrahedron Lett. 2010, 51, 1287.
[18] (a) Peng, H.-H.; Xi, Y.-M.; Ronaghi, N.; Dong, B.-L.; Akhmedov, N. G.; Shi, X.-D. J. Am. Chem. Soc. 2014, 136, 13174.
(b) Vilhanová, B.; Václavík, J.; Artiglia, L.; Ranocchiari, M.; Togni, A.; Bokhoven, J. A. ACS Catal. 2017, 7, 3414.
[19] Lampkowski, J. S.; Uthappa, D. M.; Halonski, J. F.; Maza, J. C.; Young, D. D. J. Org. Chem. 2016, 81, 12520.
[20] Su, L.-B.; Dong, J.-Y.; Liu, L.; Sun, M.-L.; Qiu, R.-H.; Zhou, Y.-B.; Yin, S.-F. J. Am. Chem. Soc. 2016, 138, 12348.
[21] Wan, J.-P.; Cao, S.; Jing, Y.-F. Appl. Organomet. Chem. 2014, 28, 631.
[22] Yang, X.; Matsuo, D.; Suzuma, Y.; Fang, J.-K.; Xu, F.; Orita, A.; Otera, J. Synlett 2011, 2402.
[23] Peng, L.-F.; Xu, F.; Suzuma, Y.; Orita, A.; Otera, J. J. Org. Chem. 2013, 78, 12802.
[24] Peng, L.-F.; Xu, F.; Shinohara, K.; Orita, A.; Otera, J. Chem. Lett. 2014, 43, 1610.
[25] Peng, L.-F.; Xu, F.; Shinohara, K.; Orita, A.; Otera, J. Org. Chem. Front. 2015, 2, 248.

膦酰保护基促进选择性Hay偶联制备非对称1,3-二炔

Phosphoryl Protecting Group Enabled Facile Synthesis of Unsymmetrical 1,3-Diynes by Selective Hay Coupling

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 12

编辑推荐

相关统计

本文评价

[1]	王银银, 林晓婉, 张飘, 沈美华, 徐华栋, 徐德锋. 基于吡啶和1,3,5-三嗪的PNP钳状配体的设计合成以及在钴催化的末端炔烃半氢化反应中的应用[J]. 有机化学, 2021, 41(8): 3312-3320.
[2]	胡志芳, 彭丽芬, 邱仁华, 折田明浩. 末端炔烃保护基的研究进展[J]. 有机化学, 2020, 40(10): 3112-3119.
[3]	戚海棠, 宋光琳, 权正军, 王喜存. CuSO₄·5H₂O/NaAsc催化下碘代芳烃和末端炔烃的Sonogashira偶联反应[J]. 有机化学, 2017, 37(7): 1855-1859.
[4]	关志朋, 师瑶, 石炜, 陈浩. 温和条件下去丙酮保护制备末端单炔烃及末端二炔的方法[J]. 有机化学, 2017, 37(2): 418-422.
[5]	李福卫, 王小龙, 于海涛. 铜催化腙酰卤与端炔的串联反应制备1,3,5-三取代吡唑衍生物[J]. 有机化学, 2016, 36(5): 1127-1132.
[6]	李亦彪, 程亮, 陈路, 李滨, 孙宁, 卿宁. 基于末端炔烃一锅法合成取代噻吩和呋喃化合物[J]. 有机化学, 2016, 36(10): 2426-2436.
[7]	王翔^a,b; 赖媛媛^a,c ; 吴宏^a; 张建明^a ; 李永建^*,a. 金催化的吲哚与末端炔烃的分子间烷基化反应[J]. 有机化学, 2009, 29(03): 432-436.
[8]	陶李明,梁云,李金恒^{a. 末端炔烃二聚反应合成共轭烯炔的研究进展[J]. 有机化学, 2007, 27(9): 1078-1086.}
[9]	王阿忠,江焕峰. 超临界二氧化碳中PdCl₂-CuCl₂体系催化末端炔烃氧化偶联反应[J]. 有机化学, 2007, 27(05): 619-622.
[10]	石启英. Pd(PPh₃)₂Cl₂-CuCl体系催化有机高价碘杂环化合物与末端炔烃的化学选择性交叉偶联反应[J]. 有机化学, 2004, 24(8): 912-915.
[11]	谢叶香, 李金恒, 尹笃林, 江焕峰. 超临界二氧化碳介质中钯催化炔烃羰基化反应[J]. 有机化学, 2004, 24(2): 169-172.
[12]	司玉贵, 黄浩, 姜标. 末端炔烃对碳氧和碳氮双键的加成反应[J]. 有机化学, 2004, 24(11): 1389-1395.