Progress of Nucleophilic Substitution of Allylic Alcohols

doi:10.6023/cjoc201505006

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2049-2058.DOI: 10.6023/cjoc201505006 Previous Articles Next Articles

Reviews

烯丙醇在亲核取代反应中的研究进展

张小祥^a, 孙小萍^a, 谈继淮^a, 樊辉^b, 饶卫东^a

a 南京林业大学化工学院江苏省生物质绿色燃料与化学品重点实验室南京 210037;
b 常州大学石油化工学院常州 213164

收稿日期:2015-05-05 修回日期:2015-06-05 发布日期:2015-06-19
通讯作者: 张小祥, 饶卫东 E-mail:s070038@hotmail.com;wdrao15@163.com
基金资助:
国家自然科学青年基金(No. 21302096 )、江苏省自然科学青年基金(No. BK20130962)、江苏高校优势学科建设工程(PAPD)资助项目.

Progress of Nucleophilic Substitution of Allylic Alcohols

Zhang Xiaoxiang^a, Sun Xiaoping^a, Tan Jihuai^a, Fan Hui^b, Rao Weidong^a

a Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
b School of Petrochemical Engineering, Changzhou University, Changzhou 213164

Received:2015-05-05 Revised:2015-06-05 Published:2015-06-19
Supported by:
Project supported by the Young National Natural Science Foundation of China Grant (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (No. BK20130962) and the Project Fund from the Priority Academic Program Development of Jiangsu Higher, Education Institutions (PAPD).

Nucleophilic substitution of allylic alcohols is very important in organic synthetic chemistry, which could be used for the synthesis of bioactive pharmaceutic compounds and natural compounds. One of the most powerful and efficient methods to introduce a C-3 unit is the allylic reaction. The advantage of this synthetic approach is the retention of the C＝C bond in the product that can act as a handle for further functional group transformations. One synthetic strategy that has been often relied upon to introduce this functional group is the Tsuji-Trost reaction. However, a drawback of this method is the generation of waste products resulting from displacement of the leaving group on treating with a catalyst and/or nucleophile. Therefore, the direct allylation of allylic alcohols is considered as a green method. In this review, the latest research progress on the Lewis and Brønsted acids catalyzed intermolecular and intramolecular nucleophilic substitution for the formation of C—X (X＝C, N, O, S) bond is presented, and a variety of nucleophiles, such as aromatical compounds, carbonyl compounds, amines or sulfonamides, alcohols and so on, are discussed. Finally, the problems and difficulties in research and application of allylation are discussed and then prospective is provided.

Key words: allylic alcohols, nucleophilic substitution, homogeneus catalyzed, allylation

Cite this article

Zhang Xiaoxiang, Sun Xiaoping, Tan Jihuai, Fan Hui, Rao Weidong. Progress of Nucleophilic Substitution of Allylic Alcohols[J]. Chin. J. Org. Chem., 2015, 35(10): 2049-2058.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Tsuji, J. Transition Metal Reagents and Catalysts, Wiley, New York, 2000.
[2] (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144.(b) Trost, B. M. Tetrahedron 1977, 33, 2615.(c) Trost, B. M. Acc. Chem. Res. 1980, 13, 385.(d) Trost, B. M.; Verhoeven, T. R. Comprehensioe Organometallic Chemistry; Pergamon: Oxford, 1982, pp. 799～938.(e) Trost, B. M. J. Organomet. Chem. 1986, 300, 263.
[3] For reviews on allylation, see: (a) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2013, 113, 5595. (b) Mejuch, T.; Gilboa, N.; Gayon, E.; Wang, H.; Houk, K. N.; Marek, I. Acc. Chem. Res. 2013, 46, 1659. (c) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774. (d) Tietze, L. F.; Kinzel, T.; Brazel, C. C. Acc. Chem. Res. 2009, 42, 367. For selected examples on allylation, see: (e) Tao, Z.-L.; Li, X.-H.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 4054. (f) Deng, H.-P.; Wang, D.; Szabó, K. J. J. Org. Chem. 2015, 80, 3343.(g) Feng, T.; Si, C.; Liu, R.; Fan, X.; Wei, B. Chin. J. Org. Chem. 2013, 33, 1291 (in Chinese).(冯涛, 司长梅, 刘如成, 范翔, 魏邦国, 有机化学, 2013, 33, 1291.) (h) Min, Q.-Q.; Yin, Z.; Feng, Z.; Guo, W.-H.; Zhang, X. J. Am. Chem. Soc. 2014, 136, 1230.(i) Chen, W.; Chen, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 15825.(j) Sheffy, F. K.; Godschalx, J. P.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4833. (k) Godschalx, J. P.; Stille, J. K. Tetrahedron Lett. 1980, 21, 2599. (l) Moreno-Manas, M.; Pajuelo, F.; Pleixats, R. J. Org. Chem. 1995, 60, 2396. (m) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972. (n) Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581. (o) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179.
[4] Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
[5] Bandini, M.; Tragni, M. Org. Biomol. Chem. 2009, 7, 1501.
[6] Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L., Jr.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411.
[7] Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 6, 4387.
[8] Tsuchimoto, T.; Tobita, K.; Hiyama,T.; Fukuzawa, S. J. Org. Chem. 1997, 62, 6997.
[9] Piao, C. R.; Zhao, Y. L.; Han, X. D.; Liu, Q. J. Org. Chem. 2008, 73, 2264.
[10] Zhang, X.; Rao, W.; Sally; Chan, P. W. H. Org. Biomol. Chem. 2009, 7, 4186.
[11] Rao, W.; Chan, P. W. H. Org. Biomol. Chem. 2008, 6, 2426.
[12] Chen, Y.; Lu, Y.; Li, G.; Liu, Y. Org. Lett. 2009, 11, 3838.
[13] McCubbin, J. A.; Hosseini, H.; Krokhin, O. V. J. Org. Chem. 2010, 75, 959.
[14] Niggemann, M.; Meel, M. J. Angew. Chem., Int. Ed. 2010, 49, 3684.
[15] Davies, H. J. Appl. Chem. 1959, 9, 137.
[16] Sanz, R.; Martínez, A.; Miguel, D.; Álvarez-Gutiérrez, J. M.; Rodríguez, F. Adv. Synth. Catal. 2006, 348, 1841.
[17] Bras, J. L.; Muzart, J. Tetrahedron 2007, 63, 7942.
[18] Liu, Y. L.; Liu, L.; Wang, Y. L.; Han, Y. C. Wang, D.; Chen, Y. J. Green Chem. 2008, 10, 635.
[19] Yasuda, M.; Somyo, T.; Baba, A. Angew. Chem., Int. Ed. 2006, 45, 793.
[20] Yadav, J. S.; Subba Reddy, B. V.; Aravind, S.; Narayana Kumar, G. G. K. S.; Reddy, A. S. Tetrahedron Lett. 2007, 48, 6117.
[21] Jana, U.; Maiti, S.; Biswas, S. Tetrahedron Lett. 2007, 48, 7160.
[22] Zhou, X.; Zhang, H.; Xie, X.; Li, Y. J. Org. Chem. 2008, 73, 3958.
[23] Guo, S.; Liu, Y. Org. Biomol. Chem. 2008, 6, 2064.
[24] Wang, J.; Zhang, L.; Jing, Y.; Huang, W.; Zhou, X. Tetrahedron Lett. 2009, 50, 4978.
[25] Namba, K.; Yamamoto, H.; Sasaki, I.; Mori, K.; Imagawa, H.; Nishizawa, M. Org. Lett. 2008, 10, 1767.
[26] Bandini, M.; Eichholzer, A.; Kotrusz, P.; Tragni, M.; Troisi, S.; Umani-Ronchi, A. Adv. Synth. Catal. 2009, 351, 319.
[27] Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9533.
[28] Yasuda, M.; Somyo, T.; Baba, A. Angew. Chem., Int. Ed. 2006, 45, 793.
[29] Rueping, M.; Nachtsheim, B. J.; Kuenkel, A. Org. Lett. 2007, 9, 825.
[30] Noji, M.; Konno, Y.; Ishii, K. J. Org. Chem. 2007, 72, 5161.
[31] Huang, W.; Wang, J.; Shen, Q.; Zhou, X. Tetrahedron Lett. 2007, 48, 3969.
[32] Jana, U.; Biswas, S.; Maiti, S. Tetrahedron Lett. 2007, 48, 4065.
[33] Rao, W.; Tay, A. H. L.; Goh, P. J.; Choy, J. M. L.; Ke, J. K.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 122.
[34] Shibuya, R.; Lin, L.; Nakahara, Y.; Mashima, K.; Ohshima, T. Angew. Chem., Int. Ed. 2014, 53, 4377.
[35] Huo, X.; Yang, G.; Liu, D.; Liu, Y.; Gridnev, I. D.; Zhang, W. Angew. Chem., Int. Ed. 2014, 53, 6776.
[36] Xie, Y.; Floreancig, P. E. Angew. Chem., Int. Ed. 2014, 53, 4926.
[37] Qin, H.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2007, 119, 413.
[38] Guo, S.; Song, F.; Liu, Y. Synlett 2007, 964.
[39] Wu, W.; Rao, W.; Er, Y. Q.; Loh, J. K.; Poh, C.Y.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 2620.
[40] Mukherjee, P.; Widenhoefer, R. A. Org. Lett. 2010, 12, 1184.
[41] Shu, X.; Liu, X.; Xiao, H.; Ji, K.; Guo, L.; Liang, Y. Adv. Synth. Catal. 2008, 350, 243.
[42] Lu, Y.; Fu, X.; Chen, H.; Du, X.; Jia, X.; Liu, Y. Adv. Synth. Catal. 2009, 351, 129.
[43] Bauer, J. M.; Frey, W.; Peters, R. Angew. Chem., Int. Ed., 2014, 53, 7634.
[44] Zhang, X.; Teo, J. W.; Ma, D. L.; Leung, C. H.; Chan, P. W. H. Tetrahedron Lett. 2014, 55, 6703.
[45] Namba, K.; Nakagawa. Y.; Yamamoto, H.; Imagawa, H.; Nishizawa, M. Synlett 2008, 1719.
[46] Yamamoto, H.; Ho, E.; Namba, K.; Imagawa, H.; Nishizawa, M. Chem.-Eur. J. 2010, 16, 11271.
[47] Guérinot, A.; Serra-Muns, A.; Gnamm, C.; Bensoussan, C.; Reymond, S.; Cossy, J. Org. Lett. 2010, 12, 1808.
[48] Mukherjee, P.; Widenhoefer, R. A. Org. Lett. 2011, 13, 1334.
[49] Kawai, N.; Abe, R.; Matsuda, M.; Uenishi, J. J. Org. Chem. 2011, 76, 2102.
[50] Kothandaraman, P.; Foo, S. J.; Chan, P. W. H. J. Org. Chem. 2009, 74, 5947.
[51] Aponick, A.; Li, C.-Y.; Biannic, B. Org. Lett. 2008, 10, 669.
[52] Aponick, A.; Biannic, B.; Jong, M. R. Chem. Commun. 2010, 46, 6849.
[53] Bandini, M.; Monari, M.; Romaniello, A.; Tragni, M. Chem.-Eur. J. 2010, 16, 14272.
[54] Aponick, A.; Biannic, B. Org. Lett. 2011, 13, 1330.
[55] Rueping, M.; Uria, U.; Lin, M. Y.; Atodiresei, I. J. Am. Chem. Soc. 2011, 133, 3732.
[56] Satoh, T.; Ikeda, M.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4877.
[57] Rao, W.; Tay, A. H. L.; Goh, P.J.; Choy, J. M. L.; Ke, J. K.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 112.

烯丙醇在亲核取代反应中的研究进展

Progress of Nucleophilic Substitution of Allylic Alcohols

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yong Zhang, Zhigao Tian, Lin Huang, Qiufei Hou, Honghong Fan, Wanqiang Wang. Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 561-572.
[2]	Zhiyou Huang, Ping Yang, Bo He, Wenxia Ou, Siyu Yuan. Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 309-315.
[3]	Leigang Wang, Yixuan Zheng, Xi Zhou, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fener Chen. Synthesis of α-Aryl Nitriles via Nucleophilic Substitution of α-Cyanohydrin Methanesulfonates with Malonates [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 668-678.
[4]	Yudong Li, Ying Li, Ya'nan Dong, Chungu Xia, Yuehui Li. Manganese-Catalyzed Allylation of Quinazolinones with 4-Vinyl-1,3-dioxolan-2-one via C—H Activation [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 847-853.
[5]	Feng Wang, Danfeng Huang, Pengfei Zhao, Ming Yang, Tongyu Han, Kehu Wang, Junjiao Wang, Yingpeng Su, Yulai Hu. Study on the Allylation of Benzol[e][1,2,3]oxathiazine-2,2-dioxides [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 507-518.
[6]	Yaohui Xu, Zhen Wu, Xinxin Wu, Chen Zhu. Transition-Metal Free Radical-Mediated C—H Bond Alkynylation and Allylation of Ethers, Aldehydes and Amides [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4340-4349.
[7]	Jiazhuang Wang, Liguo Teng, Shaoqi Xiong, Tiebo Xiao, Yubo Jiang. Rh-Catalyzed gem-Difluoroallylation of N-Tosylhydrazones [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3658-3667.
[8]	Yuan Zhu, Leyuan Chen, Wenbin Hou, Yiliang Li. Recent Progress in Nucleophilic Fluoride Mediated Fluorine-18 Labeling of Arenes and Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1774-1788.
[9]	Yu Wang, Jingyang Wang, Xiaoyu Wu, Guangni Ding, Zhaoguo Zhang, Xiaomin Xie. Advances in Deallylation [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1337-1358.
[10]	Boshi Han, Zheng Shi, Huihong He, Xinghua Zhang. Study on the Copper-Catalyzed Selective Allylation of Aryl (or Alkyl) Halides [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 695-701.
[11]	Jiahao Liu, Shidong Zhang, Zihong Luan, Yan Liu, Zhuofeng Ke. Ruthenium Catalyzed Selective Acceptorless Dehydrogenation of Allylic Alcohols to α,β-Unsaturated Carbonyls [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4361-4369.
[12]	Xinling Li, Huili Liu, Shunji Zhang. Direct Nucleophilic Substitution of Propargyl Alcohols with Enoxysilanes [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 407-411.
[13]	Ma Xiantao, Yu Jing, Wang Zilong, Zhang Yun, Zhou Qiuju. Efficient Activation of Allylic Alcohols in Pd-Catalyzed Allylic Substitution Reactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2669-2677.
[14]	Liu Na, Guo Siqi, Liu Junfang, Chen Yantao, Xu Xiaoming, Zhang Jing, Kang Yaqing, Luo Cheng, Chen Shijie, Chen Hua. Design, Synthesis, and Biological Activities of Novel Triazolothiadiazole Derivatives Linked with Amino Side Chain Containing Urea Group as DOT1L Inhibitors [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2450-2459.
[15]	Li Ruoxin, Han Rui, Gao Jinming. Synthesis of Key Intermediate of Cyathane Diterpenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2148-2152.