脱氢偶联制备芳基醚方法的研究进展

doi:10.6023/cjoc201904011

摘要/Abstract

芳香醚结构是许多天然产物以及药物分子的重要骨架, 同时也是非常重要的有机合成中间体. 通常, 芳香醚由含离去官能团的芳烃与醇或酚偶联制得. 此类方法由于需对底物进行预官能团化, 因此存在着低原子及步骤经济性不足等问题. 近年来, 利用过渡金属催化的C—H键活化策略, 通过芳烃与醇或酚的脱氢偶联实现芳基醚的制备, 越来越受到有机化学家关注. 综述了最近通过脱氢偶联制备芳香醚化合物的研究进展. 围绕各类方法的底物适应范围和反应机理等进行详细论述, 并就该领域的局限性和未来的发展前景进行总结和展望.

关键词: 芳香醚, 脱氢偶联, C—H键活化, 苯酚, 醇

Aryl ethers are important central motifs that are abundant in many natural products and drug molecules, as well as versatile building blocks for organic synthesis. Aryl ethers were usually synthesized through the coupling reactions between leaving group substituted arenes and alcohols. However, the introduction of leaving group requires extra synthetic operation and produces lots of wastes. Over the past decade, the method for the synthesis of aryl ethers via C—H alkoxylation or aryloxylation has received much attention due to its potential as an atom and step efficient methodology. Herein, the research advances on the synthesis of aryl ethers through dehydrogenative coupling are reviewed. The detailed substrate scopes and reaction mechanisms, as well as the limitations of current procedures and the prospects for the future, are discussed.

Key words: aryl ether, dehydrogenative coupling, C—H activation, phenol, alcohol

引用此文

唐灏, 骆钧飞, 解攀. 脱氢偶联制备芳基醚方法的研究进展[J]. 有机化学, 2019, 39(10): 2735-2743.

Tang Hao, Luo Junfei, Xie Pan. Advances on the Synthesis of Aryl Ethers via Dehydrogenative Coupling[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2735-2743.

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图/表 12

图1. 含芳香醚结构的重要分子

Figure 1. Important molecules containing aryl ethers

图式1. 芳基醚制备方法

Scheme 1. Methods for the preparation of aryl ethers

图式2. Pd催化C—H活化制备芳基醚机理

Scheme 2. Mechanism for the synthesis of aryl ethers via Pd- catalyzed C—H activation

图式3. 钯催化的C—O环化脱氢机理图式

Scheme 3. Pd-catalyzed C—O cyclization

图式4. C—H官能化反应合成二氢苯并呋喃衍生物

Scheme 4. C—H functionalization for the synthesis of dihdro- benzofuran derivatives

图式5. Cu介导C—H烷氧基化机理

Scheme 5. Mechanism for Cu-mediated C—H alkoxylation

图式6. 铜催化C—H烷氧基化催化循环图式

Scheme 6. Catalytic cycle for Cu-catalyzed C—H alkoxylation

图式7. 一价铜催化C—H甲氧基化机理图式

Scheme 7. Mechanism for Cu(I)-catalyzed C—H methoxylation.

图式8. 钴催化C—H烷氧基化催化循环图式

Scheme 8. Catalytic cycle for Co-catalyzed C—H alkoxylation

图式9. 铜催化分子内C—H芳氧基化机理图式

Scheme 9. Mechanism for Cu-catalyzed intramolecular aryloxylation.

图式10. 苯二氮?类化合物的合成

Scheme 10. Synthesis for the benzodiazepine derivative

图式11. 四丁基碘化铵催化下的芳烃分子内脱氢机理图式

Scheme 11. Ammonium tetrabutyl iodide catalyst dehydrogenative aryl intramolecular mechanism

参考文献 41

[1]	(a) Jabran, K.; Ehsanullah; Hussain, M.; Farooq, M.; Babar, M.; Doǧan, M.-N.; Lee, D.-J. Weed Biol. Manage. 2012, 12, 136.
	(b) Negro, R.; Formoso, G.; Mangieri, T.; Pezzarossa, A.; Dazzi, D.; Hassan, H. J. Clin. Endocrinol. Metab. 2006, 91, 2587.
	(c) Kosenkova, Y.-S.; Polovinka, M.; Komarova, N.; Korchagina, D.; Kurochkina, N. Y.; Cheremushkina, V.; Salakhutdinov, N. Chem. Nat. Compd. 2007, 43, 712.
	(d) Deng, H.; Jung, J.-K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 9032.
[2]	(a) Chen, G.; Du, J. Chin. J. Org. Chem. 2014, 34, 65 (in Chinese).
	( 陈国军, 杜建时, 有机化学, 2014, 34, 65 )
	(b) Tobisu, M.; Chatani, N. Acc. Chem. Res. 2015, 48, 1717.
[3]	(a) Ullmann, F.; Sponagel, P. Ber. Dtsch. Chem. Ges. 1905, 38, 2211. doi: 10.1002/(ISSN)1099-0682
	(b) Xiao, S.; Zhu, J.; Mu, X.; Li, Z. Chin. J. Org. Chem. 2013, 33, 1668 (in Chinese). doi: 10.1002/(ISSN)1099-0682
	( 肖尚友, 朱俊, 穆小静, 李正华, 有机化学, 2013, 33, 1668.) doi: 10.1002/(ISSN)1099-0682
[4]	(a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933. doi: 10.1016/S0040-4039(98)00503-6
	(b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937. doi: 10.1016/S0040-4039(98)00503-6
	(c) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415. doi: 10.1016/S0040-4039(98)00503-6
[5]	(a) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
	(b) Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770.
	(c) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109.
[6]	Terrett, J. A.; Cuthbertson, J. D.; Shurtleff, V. W MacMillan, D. W. C .; Nature 2015, 524, 330. doi: 10.1038/nature14875
[7]	(a) Yang, F.; Zhang, H.; Liu, X.; Wang, B.; Ackermann, L. Chin. J. Org. Chem. 2019, 39, 59 (in Chinese).
	( 杨帆致, 张晗, 刘旭日, 王博, Lutz, A., 有机化学, 2019, 39, 59)
	(b) Leila, R.; Asieh, Y.; Mehdi, S. ChemCatChem 2018, 10, 20.
	(c) Kamellia, N.; Sheida, A.; Mohammad, N.; Parvaneh, D. K. N.; Esmail, V. RSC Adv. 2018, 8, 19125
	(d) Bhunia, S.; Pawar, G. G.; Kumar, S. V.; Jiang, Y.; Ma, D. Angew. Chem., Int. Ed. 2017, 56, 16136
	(e) Ding, H.; Li, J.; Guo, Q.; Xiao, Y. Chin. J. Org. Chem.(in Chinese). 2017, 37, 3112
	( 丁怀伟, 李娟, 郭庆辉, 肖琰, 有机化学, 2017, 37, 3112)
[8]	Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
[9]	Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476.
[10]	Jiang, T.-S.; Wang, G.-W. J. Org. Chem. 2012, 77, 9504
[11]	Shi, S.-P.; Kuang, C.-X. J. Org. Chem. 2014, 79, 6105.
[12]	Li, W.; Sun, P.-P. J. Org. Chem. 2012, 77, 8362
[13]	Yin, Z.-W.; Jiang, X.-Q.; Sun, P.-P. J. Org. Chem. 2013, 78, 10002 doi: 10.1021/jo401623j
[14]	Zhang, C .; Sun, P.-P. J. Org. Chem. 2014, 79, 8457. doi: 10.1021/jo5014146
[15]	Gao, T.-T.; Sun, P.-P. J. Org. Chem. 2014, 79, 9888. doi: 10.1021/jo501902d
[16]	Peron, F.; Fossey, C.; Santos, J. O. S.; Cailly, T.; Fabis, F. Chem.- Eur. J. 2014, 20, 1.
[17]	Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 4187.
[18]	(a) Shen, T.; Wang, X.-N.; Lou, H.-X. Nat. Prod. Rep. 2009, 26, 916.
	(b) Veitch, N. C. Nat. Prod. Rep. 2007, 24, 417.
	(c) Watzke, A.; O'Malley, S. J.; Bergman, R. G.; Ellman, J. A. J. Nat. Prod. 2006, 69, 1231.
	(d) Tsui, G. C.; Tsoung, J.; Dougan, P.; Lautens, M. Org. Lett. 2012, 14, 5542.
[19]	Wang, X.-S.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203.
[20]	Wang, H.-B.; Li, G.; Engle, K. M.; Yu, J.-Q.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6774.
[21]	Cheng, X.-F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S Yu, J.-Q .; J. Am. Chem. Soc. 2013, 135, 1236.
[22]	Wang, Z.-L.; Zhao, L.; Wang, M.-X. Org. Lett. 2011, 13, 6560.
[23]	Zhang, L.-B.; Hao, X.-Q.; Zhang, S.-K.; Liu, K.; Ren, B.-Z.; Gong, J.-F.; Niu, J.-L.; Song, M.-P. J. Org. Chem. 2014, 79, 10399.
[24]	Bhadra, S.; Matheis, C.; Katayev, D.; Gooßen, L. J. Angew. Chem. 2013, 125, 9449.
[25]	Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842.
[26]	Yin, X.-S.; Li, Y.-C.; Yuan, J.; Gua, W.-J.; Shi, B.-F. Org. Chem. Front. 2015, 2, 119.
[27]	Zhang, L.-B.; Hao, X.-Q.; Zhang, S.-K.; Liu, Z.-J.; Zheng, X.-X.; Gong, J.-F.; Niu, J.-F.; Song, M.-P. Angew. Chem., Int. Ed. 2015, 54, 272. doi: 10.1002/(ISSN)1521-3757
[28]	Zheng, Y.-W.; Ye, P.; Chen, B.; Meng, Q.-Y.; Feng, K.; Wang, W.-G.; Wu, L.-Z.; Tung, C.-H. Org. Lett. 2017, 19, 2206.
[29]	Ohkubo, K.; Kobayashi, T.; Fukuzumi, S. Opt. Express 2012, 20, A360.
[30]	Tang, L.; Pang, Y.; Yan, Q.; Shi, L.-Q.; Huang, J.-H.; Du, Y.-F.; Zhao, K. J. Org. Chem. 2011, 76, 2744.
[31]	Xiao, B.; Gong, T.-J.; Liu, Z.-J.; Liu, J.-H.; Luo, D.-F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250.
[32]	Wei, Y.; Yoshikai, N. J. Org. Chem. 2011, 13, 5504.
[33]	Zhao, J.-J.; Wang, Y.; He, Y.-M.; Liu, L.-Y.; Zhu, Q. Org. Lett. 2012, 14, 1078.
[34]	(a) Zhao, J.-J.; Wang, Y.; Zhu, Q. Synthesis 2012, 44, 1551. doi: 10.1055/s-0031-1290966
	(b) Zhao, J.-J.; Zhang, Q.; Liu, L.-Y.; He, Y.-M.; Li, J.; Li, J.; Zhu, Q. Org. Lett. 2012, 14, 5362. doi: 10.1055/s-0031-1290966
[35]	Roane, J.; Daugulis, O. Org. Lett. 2013, 15, 5842.
[36]	Hao, X.-Q.; Chen, L.-J.; Ren, B.; Li, L.-Y.; Yang, X.-Y.; Gong, J.-F.; Niu, J.-L.; Song, M.-P. Org. Lett. 2014, 16, 1104.
[37]	Zhou, Y.-F.; Zhu, J.-M.; Li, B.; Zhang, Y.; Feng, J.; Hall, A.; Shi, J.-Y.; Zhu, W.-L. Org. Lett.. 2016, 18, 3803
[38]	Kumar, G. S.; Pieber, B.; Reddy, K. R.; Kappe, C. O. Chem.-Eur. J. 2012, 18, 6124.
[39]	Barve, B. D.; Wu, Y.-C.; El-Shazly, M.; Korinek, M.; Cheng, Y.-B.; Wang, J.-J.; Chang, F.-R. Tetrahedron 2015, 71, 2290 doi: 10.1016/j.tet.2015.02.035
[40]	Barve, B. D.; Wu, Y.-C El-Shazly, M.; Korinek, M.; Cheng, Y.-B.; Wang, J.-J.; Chang, F.-R. Org. Lett. 2014, 16, 1912.
[41]	Boominathan, S. S. K.; Hu, W.-P.; Senadi, G. C.; Vandavasia, J. K.; Wanga, J.-J. Chem. Commun. 2014, 50, 6726.