Recent Progress of Protecting Groups for Terminal Alkynes

doi:10.6023/cjoc202005094

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3112-3119.DOI: 10.6023/cjoc202005094 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

末端炔烃保护基的研究进展

胡志芳^a, 彭丽芬^a,b, 邱仁华^b, 折田明浩^c

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湖南湘潭 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;
c 日本冈山理科大学化学系日本冈山 700-0005

收稿日期:2020-05-31 修回日期:2020-07-02 发布日期:2020-07-23
通讯作者: 彭丽芬, 邱仁华 E-mail:1060137@hnust.edu.cn;renhuaqiu1@hnu.edu.cn;orita@dac.ous.ac.jp
基金资助:
国家自然科学基金（No.21802040）、湖南省自然科学基金（No.2018JJ3145）、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.E21843）资助项目.

Recent Progress of Protecting Groups for Terminal Alkynes

Hu Zhifang^a, Peng Lifen^a,b, Qiu Renhua^b, Orita Akihiro^c

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, Hunan 411201, China;
b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China;
c Department of Chemistry, Okayama University of Science, Okayama 700-0005, Japan

Received:2020-05-31 Revised:2020-07-02 Published:2020-07-23
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21802040), the Natural Science Fund Youth Project of Hunan Province (No. 2018JJ3145) and the Open Foundation of Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology (No. E21843).

The protection/deprotection of functional group is one of the fundamental technologies in organic synthesis. An ideal protecting group needs to satisfy the following issues:facile introduction, stability and facile deprotection. Protection of an acetylenic hydrogen is often necessary because of its acidity. In this review, the recent progress of protecting groups for terminal alkyne is highlighted. Based on different polarity of protecting groups, less polar protecting groups such as trimethylsilyl (TMS), trimethylgermanium group (Me₃Ge) and high polar protecting groups like (3-cyanopropyl)dimethylsilyl (CPDMS), (3-cyanopropyl)diisopropylsilyl (CPDIPS) and diphenylphosphoryl (Ph₂P(O)) are introduced in detail.

Key words: protecting group, terminal alkyne, Sonogashira coupling

Cite this article

Hu Zhifang, Peng Lifen, Qiu Renhua, Orita Akihiro. Recent Progress of Protecting Groups for Terminal Alkynes[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3112-3119.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Greene, T. W.; Wuts. P. G. M. Protective Groups in Organic Synthesis, 3th ed., John Wiley & Sons, Inc., New York, 1999.
[2] (a) Stang, P. J.; Diederich. F. Modern Acetylene Chemistry, VCH, Weinheim, 1995.
(b) Diederich, F.; Stang, P. J.; Tykwinski, R. R. Acetylene Chemistry, Willey-VCH Verlag GmbH & CO. KgaA, Weinheim, 2005.
(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.)
(d) 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.
(e) Wang, Z.; Yang, L.; Liu, H.-L.; Bao, W.-H.; Tan, Y.-Z.; Wang, M.; Tang, Z.; He, W.-M. Chin. J. Org. Chem. 2018, 38, 2639(in Chinese). (王峥, 杨柳, 刘慧兰, 谭英芝, 包文虎, 汪明, 唐子龙, 何卫民, 有机化学, 2018, 38, 2639.)
(f) 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.
(g) Li, W.-Y.; Yin, G.-X.; Huang, L.; Xiao, Y.; Fu, Z.-M.; Xin, X.; Liu, F.; Li, Z.-Z. He, W.-M. Green Chem. 2016, 18, 4879.
(h) Wu, C.; Wang, Z.; Hu, Z.; Zeng, F.; Zhang, X.-Y.; Cao, Z.; Tang, Z.;. He, W.-M.; Xu, X.-H. Org. Biomol. Chem. 2018, 16, 3177.
(i) Peng, L.-F.; Peng, C.; Wang, M.; Tang, Z.-L.; Jiao, Y.-C.; Xu, X.-H. Chin. J. Org. Chem. 2018, 38, 3048(in Chinese). (彭丽芬, 彭超, 汪明, 唐子龙, 焦银春, 许新华, 有机化学, 2018, 38, 3048.)
(j) Wu, L.; Peng, L.-F.; Hu, Z.-F.; Wang, H.; Tang, Z.-L.; Jiao Y.-C.; Xu, X.-H. J. Chem. Res. 2019, 43, 503.
[3] (a) Mao, G.; Orita, A.; Fenenko, L.; Yahiro, M.; Adachi, C.; Otera, J. Mater. Chem. Phys. 2009, 115, 378.
(b) Fenenko, L.; Shao, G.; Orita, A.; Yahiro, M.; Otera, J.; Svechnikov, S.; Adachi, C. Chem. Commun. 2007, 2278.
(c) Matsuo, D.; Yang, X.; Hamada, A.; Morimoto, K.; Kato, T.; Yahiro, M.; Adachi, C.; Orita, A.; Otera, J. Chem. Lett. 2010, 39, 1300.
(d) Oyamada, T.; Shao, G.; Uchiuzou, H.; Nakanotani, H.; Orita, A.; Otera, J.; Yahiro, M.; Adachi, C. Jpn. J. Appl. Phys., Part 2 2006, 45, 46.
(e) Yang, X.; Kajiyama, S.; Fang, J.-K.; Xu, F.; Uemura, Y.; Koumura, N.; Hara, K.; Orita, A.; Otera, J. Bull. Chem. Soc. Jpn. 2012, 85, 687.
(f) Yang, X.; Fang, J.-K.; Suzuma, Y.; Xu, F.; Orita, A.; Otera, J.; Kajiyama, S.; Koumura, N.; Hara, K. Chem. Lett. 2011, 40, 620.
(g) Peng, L.-F.; Hu, Z.-F.; Wang, H.; Wu, L.; Jiao, Y.-C.; Tang, Z.-L.; Xu, X.-H. RSC. Adv. 2020, 10232.
(h) 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.
(i) Peng, L.-F.; Li, R.-Z.; Tang, Z.-L.; Chen, J.-Y.; Yi, R.-N.; Xu, X.-H. Tetrahedron 2017, 73, 3099.
(l) 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.)
(m) Peng, L.-F.; Hu, Z.-F.; Lu, Q.-C.; Tang, Z.-L.; Jiao Y.-C.; Xu, X.-H. Chin. Chem. Lett. 2019, 30, 2151.
(n) Wu, L.; Peng, L.-F.; Hu, Z.-F.; Jiao, Y.-C.; Tang, Z.-L.; Xu, X.-H. Curr. Org. Synth. 2020, 17, 271.
[4] (a) Rankin, G. M.; Maxwell-Cameron, I.; Painter, G. F.; Larsen, D. S. J. Org. Chem. 2013, 78, 5264.
(b) Urones, B.; Gómez Arrayás, R.; Carretero, J. C. Org. Lett. 2013, 15, 1120.
(c) Balbuena, P.; Gonçalves-Pereira, R.; Jiménez Blanco, J. L.; García-Moreno, M. I.; Lesur, D.; Ortiz Mellet, C.; García Fernández, J. M. J. Org. Chem. 2013, 78, 1390.
(d) Muranaka, K.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2011, 76, 9278.
(e) Ihara, H.; Koyanagi, M.; Suginome, M. Org. Lett. 2011, 13, 2662.
(f) Liang, H.; Corey, E. J. Org. Lett. 2011, 13, 4120.
[5] (a) Palmer, C. J.; Casida, J. E. Tetrahedron Lett. 1990, 31, 2857.
(b) Andreev, A. A.; Konshin, V. V.; Komarov, N. V.; Rubin, M.; Brouwer, C.; Gevorgyan, V. Org. Lett. 2004, 6, 421.
(c) Jiang, H.; Zhu, S. Tetrahedron Lett. 2005, 46, 517.
[6] Ernst, A.; Gobbi, L.; Vasella, A. Tetrahedron Lett. 1996, 37, 7959.
[7] Höger, S.; Bonrad, K. J. Org. Chem. 2000, 65, 2243.
[8] Gaefke, G.; Höger, S. Synthesis 2008, 2155.
[9] Yang, X.; Matsuo, D.; Suzuma, Y.; Fang, J.-K.; Xu, F.; Orita, A.; Otera, J. Synlett 2011, 2402.
[10] (a) Ito, H.; Arimoto, K.; Senusui, H.O.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977.
(b) Sugita, H.; Hatanaka, Y.; Hiyama, T. Chem. Lett. 1996, 25, 379.
[11] Davidsohn, W. E.; Henry, M. C. Chem. Rev. 1967, 67, 73.
[12] (a) Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 732.
(b) Nishikawa, T.; Ino, A.; Isobe, M.; Tetrahedron 1994, 50, 1449.
(c) Scott, L. T.; Cooney, M. J.; Johnels, D. J. Am. Chem. Soc. 1990, 112, 4054.
(d) Lu, Y.-F.; Fallis, A. G. Tetrahedron Lett. 1993, 34, 3367.
(e) Nielsen, M. B.; Diederich, F. Synlett 2002, 544.
(f) Tobe, Y.; Utsumi, N.; Kawabata, K.; Naemura, K. Tetrahedron Lett. 1996, 37, 9325.
[13] Nishikawa, T.; Ino, A.; Isobe, M. Tetrahedron 1994, 50, 1449.
[14] Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874.
[15] Li, H.-B.; Petersen, J. L.; Wang, K.-K. J. Org. Chem. 2001, 66, 7804.
[16] (a) Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956.
(b) Bell, M. L.; Chiechi, R. C.; Johnson, C. A.; Kimbal, D. B.; Matzger, A.; Wan, W. B.; Weakley, T. J. R.; Haley, M. M. Tetrahedron 2001, 57, 3507.
[17] (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
(b) Tohda, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1977, 777.
(c) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
[18] Peng, L.-F.; Xu, F.; Suzuma, Y.; Orita, A.; Otera, J. J. Org. Chem. 2013, 78, 12802.
[19] Peng, L.-F.; Xu, F.; Shinohara, K.; Orita, A.; Otera, J. Chem. Lett. 2014, 43, 1610.
[20] Tahara, K.; Furukawa, S.; Uji-i, H.; Uchino, T.; Ichikawa, T.; Zhang, J.; Mandouh, W.; Sonoda, M.; Schryver, F. C. D.; Feyter, S. D.; Tobe, Y. J. Am. Chem. Soc. 2006, 128, 16613.
[21] (a) Peña-López, M.; Ayán-Varela, M.; Sarandeses, L. A.; Sestelo, J. P. Chem. Eur. J. 2010, 16, 9905.
(b) Dogan, J.; Schulte, J. B.; Swiegers, G. F.; Wild, S. B. J. Org. Chem. 2000, 65, 951.
(c) Lu, E.; Chen, Y.; Zhou, J.; Leng, X. Organometallics 2012, 31, 4574.
[22] (a) Kosugi, M.; Fugami, K. Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.:Negishi, E., Wiley, New York, 2002.
(b) Tsuji, J. Palladium Reagents and Catalysts, Wiley, Chichester, U. K. 2004.
(c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
[23] Warner, B. P.; Buchwald, S. L. J. Org. Chem. 1994, 59, 5822.
[24] (a) Mössinger, D.; Jester, S. S.; Sigmund, E.; Müller, U.; Höger, S. Macromolecules 2009, 42, 7974.
(b) Nicolaou, K. C.; Zipkin,R. E.; Petasis, N. A. J. Am. Chem. Soc. 1982, 104, 5558.
[25] Peña-López, M.; Ayán-Varela, M.; Sarandeses, L. A.; Sestelo, J. P. Chem. Eur. J. 2010, 16, 9905.
[26] (a) Peng, L.-F.; Xu, F.; Shinohara, K.; Orita, A.; Otera, J. Org. Chem. Front. 2015, 2, 248.
(b) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Chem. Commun. 1997, 1039.
(c) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Chem. Lett. 1997, 26, 1233.
(d) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.

末端炔烃保护基的研究进展

Recent Progress of Protecting Groups for Terminal Alkynes

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Chunming Gui, Tongyao Zhou, Haifeng Wang, Qiongjiao Yan, Wei Wang, Jin Huang, Fener Chen. Recent Advances in Visible Light Photoredox-Catalyzed Alkynylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2647-2663.
[2]	Fei Chen, Sheng Tao, Ning Liu, Bin Dai. CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO₂ at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2471-2480.
[3]	Liwen Ma, Xiaoye Wei, Zilin Zhao, Ang Zhao, Xiangwen Deng, Bingnan Huo, Gang Ma, Chunfang Zhang. Theoretical Study on the Catalytic Mechanism of Copper with Various Valence for the Terminal Alkyne Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1811-1819.
[4]	Yinyin Wang, Xiaowan Lin, Piao Zhang, Meihua Shen, Huadong Xu, Defeng Xu. Design and Synthesis of Pyridine and 1,3,5-Triazine PNP Pincer Ligands and Their Application in Cobalt Catalyzed Semihydrogenation of Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3312-3320.
[5]	Jinyan Wang, Liying Dong, Ya'ni Liu, Xitong Chen, Yannan Ma, Hao Yin, Shanshan Du, Yunkun Qi, Kewei Wang. Efficient Synthesis and Oxidative Folding Studies of Centipede Toxin RhTx [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2800-2809.
[6]	Jingru Liang, Bingying Wang, Chengyin Huang, Xiaojun Ye, Yanmei Wen. Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by One-Pot Method [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2116-2120.
[7]	Peng Zhou, Shangwei Feng, Huihua Qiu, Jiantao Zhang. Sodiump-Toluenesulfinate/KI-Mediated Aerobic Oxidative Iodination of Terminal Alkynes for Synthesis of 1-Iodoalkynes and 1,3-Diynes [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 394-399.
[8]	Yao Ming, Zhang Jingjing, Yang Sen, Xiong Hangxing. γ-Aluminum Oxide-Mediated Iodination of Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2153-2158.
[9]	Wang, Yaqi, Yin, Qiang, Guo, Dun, Han, Limin, Sun, Qi, Hong, Hailong, Suo, Quanling, Suo. Quanling. Carbonyl Cobalt-Catalyzed Cyclotrimerization of Terminal Alkynes in Supercritical Carbon Dioxide [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2898-2905.
[10]	Ma Nan, Zeng Xianghua. Cu₂O-Catalyzed Green Oxidative Terminal Alkynes Homocoupling without Bases [J]. Chin. J. Org. Chem., 2018, 38(6): 1556-1561.
[11]	Kong Shengnan, Malik Abaid Ullah, Qian Xuefeng, Shu Mouhai, Xiao Wende. C-C Coupling Reactions in Water Catalyzed by Palladium [J]. Chin. J. Org. Chem., 2018, 38(2): 432-442.
[12]	Peng Lifen, Zhang Siwei, Wang Binghao, Xun Mengshuo, Tang Zilong, Jiao Yinchun, Xu Xinhua. Synthesis of Cyclic Phenyl Polyynes: Ph₂P-Deprotection/Intramolecular Eglington Coupling Cyclization [J]. Chin. J. Org. Chem., 2018, 38(2): 519-525.
[13]	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.
[14]	Qi Haitang, Song Guanglin, Quan Zhengjun, Wang Xicun. CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes [J]. Chin. J. Org. Chem., 2017, 37(7): 1855-1859.
[15]	Guan Zhipeng, Shi Yao, Shi Wei, Chen Hao. Synthesis of Terminal Alkynes/Diynes through Deprotection of Acetone Protected Alkynes under Mild Conditions [J]. Chin. J. Org. Chem., 2017, 37(2): 418-422.