呜拉嗪及其衍生物的合成研究进展

doi:10.6023/cjoc202306020

摘要/Abstract

稠环芳烃具有独特的电子性质和光学性质, 在有机光电材料领域应用广泛. 向稠环芳烃骨架中引入杂原子可改变其电子结构, 进而改变其物理、化学、光、电和磁等性质. 在众多的杂原子中, 氮原子是稠环芳烃中最常见的掺杂原子. 呜拉嗪是芘的等电子体, 又称吲哚并[6,5,4,3-ija]喹啉, 是一种新型氮杂稠环芳烃. 近年来, 呜拉嗪在染料敏化太阳能电池等领域表现出了潜在应用, 随后有关呜拉嗪的合成方法研究备受关注. 总结了近年来呜拉嗪及其衍生物的主要合成方法.

关键词: 呜拉嗪, 杂芳烃, 稠环芳烃

Polycyclic aromatic hydrocarbons (PAHs) have been widely used in the field of organic electronics, due to their unique electronic and optical properties. Doping heteroatom is a popular way to modify the electronic structures and the properties of the PAHs. The resulting heteroaromatics exihit tunable physicochemical, optical, and electrochemical properties. Among the heteroatoms embedded in the scaffold of PAHs, nitrogen atom is the most common one. Ullazine, also known as indolizino[6,5,4,3-ija]quinoline, is isoelectronic with pyrene. In recent years, ullazine and its derivatives have drawn a lot attention due to its outstanding performance in dye-sensitized solar cells. The synthesis methods of ullazine developed in recent years are presented, and the overview of the current available synthetic methods of ullazine is summarized in detail.

Key words: ullazine, heteroaromatics, polycyclic aromatic hydrocarbons

引用此文

邵梓萌, 王原辉, 王海滢, 崔培培, 刘旭光. 呜拉嗪及其衍生物的合成研究进展[J]. 有机化学, 2023, 43(11): 3679-3694.

Zimeng Shao, Yuanhui Wang, Haiying Wang, Peipei Cui, Xuguang Liu. Recent Advance in the Synthesis of Ullazine and Its Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3679-3694.

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

分享此文

图/表 24

图1. 吲哚并[3-ija]喹啉(呜拉嗪)

Figure 1. Indolizino[3-ija]quinoline (ullazine)

图式1. Balli和Zeller等利用Friedel-Crafts烷基化方法首次合成呜拉嗪及其关键步骤的反应机理

Scheme 1. Synthesis of ullazine by Balli and Zeller et al. using Friedel-Crafts alkylation and the mechanisms of key steps

图式2. 任红军课题组利用Friedel-Crafts芳基化方法合成双苯并呜拉嗪及其关键步骤的反应机理

Scheme 2. Synthesis of dibenzo[d,k]ullazines by Hongjun Ren?s group using Friedel-Crafts arylation and the mechanisms of key step

图式3. Takahashi课题组报道的铬催化的炔烃环化反应合成呜拉嗪

Scheme 3. Synthesis of ullazine by chromium-mediated alkyne benzannulation developed by Tamotsu Takahashi?s group

图式4. Gr?tzel课题组报道的铟催化炔烃环化反应合成呜拉嗪

Scheme 4. Synthesis of ullazine by indium(III) chloride-mediated alkyne benzannulation developed by Gr?tzel?s group

图式5. Nazeeruddin课题组报道的呜拉嗪的改进合成方法

Scheme 5. Improved synthesis of ullazine by Nazeeruddin?s group

图式6. Delcamp课题由报道的基于呜拉嗪的Vilsmeier-Haack反应

Scheme 6. Functionalization ullazine through Vilsmeier-Haack reaction reported by Delcamp?s group

图式7. 游劲松课题组报道的钯催化C—H官能团化方法合成π-共轭呜拉嗪

Scheme 7. Synthesis of ullazine through C—H bond functionalization reaction reported by Jinsong You?s group

图式8. 钯催化C—H官能团化方法合成π-共轭呜拉嗪的反应机理

Scheme 8. Mechanism of synthesis of ullazine through C—H bond functionalization reaction

图式9. K?nig课题组报道的光催化反应合成呜拉嗪

Scheme 9. Synthesis of ullazine through visible light mediated twofold annulation reaction reported by K?nig?s group

图式10. K?nig课题组报道的光催化反应合成呜拉嗪的机理

Scheme 10. Mechanism of visible light mediated annulation to ullazine reported by K?nig?s group

图式11. 高戈课题组报道的钯催化的苯炔环化反应合成呜拉嗪

Scheme 11. Synthesis of ullazine through aryne benzannulation reported by Ge Gao?s group

图式12. 钯催化苯炔参与的环化反应合成呜拉嗪的机理

Scheme 12. Mechanism of synthesis of ullazine through alkyne benzannulation

图式13. Müllen和冯新亮等报道的多环芳香族亚甲胺叶立德参与的[3+2]环加成方法合成呜拉嗪

Scheme 13. Synthesis of ullazine through [3+2] cycloaddition reaction reported by Müllen and Feng et al.

图式14. Ito和Nozaki等利用多环芳香族亚甲胺叶立德的[3+2]反应合成嵌有呜拉嗪的碗烯

Scheme 14. Synthesis of ullazine-embedded corannulene through [3+2] cycloaddition reaction reported by Ito and Nozaki et al.

图式15. 王娇炳课题组报道的呜拉嗪的合成

Scheme 15. Synthesis of ullazine reported by Jiaobing Wang?s group

图式16. 王娇炳课题组报道的含有呜拉嗪的螺烯的合成

Scheme 16. Synthesis of ullazine-based helicene reported by Jiaobing Wang?s group

图式17. Morin课题组报道光照脱氯化氢反应合成呜拉嗪及其D-A聚合物

Scheme 17. Synthesis of ullazine and related D-A polymers through photochemical cyclodehydrochlorination reaction reported by Morin?s group

图式18. Morin课题组报道的光照脱氯化氢方法合成含有呜拉嗪的线性和螺旋石墨烯纳米带

Scheme 18. Synthesis of ullazine-embedded linear and helical graphene nanoribbons through photochemical cyclodehydrochlorination reaction reported by Morin?s group

图式19. St?pień课题组报道的金属催化的直接芳基化反应合成呜拉嗪衍生物

Scheme 19. Synthesis of ullazine derivatives through metal catalyzed direct arylation reaction reported by St?pień?s group

图式20. Marcin St?pień课题组报道的1,3-偶极环加成反应合成呜拉嗪衍生物

Scheme 20. Synthesis of ullazine derivatives through 1,3-diplor cycloaddition reaction reported by Marcin St?pień?s group

图式21. 周旺课题组报道的铑催化的两步反应反应合成四取代呜拉嗪衍生物

Scheme 21. Synthesis of tetra-substituted ullazine derivatives through Rh-catalyzed two-step sequences reported by Wang Zhou?s group

图2. 杂原子掺杂的呜拉嗪衍生物

Figure 2. Heteroatom-doped ullazine derivatives

图3. 硼杂呜拉嗪

Figure 3. Boron-doped ullazine derivatives

参考文献 41

[1]	Cebrián, C. J. Mater. Chem. C 2018, 6(44), 11943. doi: 10.1039/C8TC03573C
[2]	Bunz, U. H. F. Acc. Chem. Res. 2015, 48(6), 1676. doi: 10.1021/acs.accounts.5b00118
[3]	Takase, M.; Enkelmann, V.; Sebastiani, D.; Baumgarten, M.; Müllen, K. Angew. Chem. Int. Ed. 2007, 46(29), 5524. doi: 10.1002/anie.v46:29
[4]	Balli, H.; Zeller, M. Helv. Chim. Acta. 1983, 66(7), 2135. doi: 10.1002/hlca.v66:7
[5]	Zhou, J.; Yang, W. J.; Wang, B. J.; Ren, H. J. Angew. Chem. Int. Ed. 2012, 51(49), 12293. doi: 10.1002/anie.201206578 pmid: 23124928
[6]	Kanno, K. I.; Liu, Y. H.; Iesato, A.; Nakajima, K.; Takahashi, T. Org. Lett. 2005, 7(24), 5453. doi: 10.1021/ol052214x
[7]	Delcamp, J. H.; Yella, A.; Holcombe, T.W.; Nazeeruddin, M. K.; Grätzel, M. Angew. Chem. Int. Ed. 2013, 52(1), 376. doi: 10.1002/anie.201205007 pmid: 22927088
[8]	Nazeeruddin, M. K.; Drigo, N.; Sanghyun, P.; Huckaba, A.; Schouwink, P.; Tabet, N. Chem.-Eur. J. 2017, 23(68), 17209. doi: 10.1002/chem.v23.68
[9]	Zhang, Y. B.; Cheema, H.; McNamara, L.; Hunt, L. A.; Hammer, N.; Delcamp, J. H. Chem.-Eur. J. 2018, 24(22), 5939. doi: 10.1002/chem.v24.22
[10]	Wan, D. Y.; Li, X. Y.; Jiang, R. Y.; Feng, B. Y.; Lan, J. B.; Wang, R. L.; You, J. S. Org. Lett. 2016, 18(12), 2876. doi: 10.1021/acs.orglett.6b01182
[11]	Larock, R. C.; Doty, M. J.; Han, X.J. Tetrahedron Lett. 1998, 39(29), 5143. doi: 10.1016/S0040-4039(98)00982-4
[12]	Das, A.; Ghosh, I.; König, B. Chem. Commun. 2016, 52(56), 8695. doi: 10.1039/C6CC04366F
[13]	Wang, D. P.; Liu, Y.; Wang, L. H.; Cheng, H.; Zhang, Y. M.; Gao, G. Chin. Chem. Lett. 2020, 32(4), 1407. doi: 10.1016/j.cclet.2020.09.057
[14]	Berger, R.; Wagner, M.; Feng, X. L.; Müllen, K. Chem. Sci. 2015, 6(1), 436. doi: 10.1039/C4SC02793K
[15]	Berger, R.; Giannakopoulos, A.; Ravat, P.; Wagner, M.; Beljonne, D.; Feng, X. L.; Müllen, K. Angew. Chem. Int. Ed. 2014, 53(39), 10520. doi: 10.1002/anie.v53.39
[16]	Ito, S.; Tokimaru, Y.; Nozaki, K. Chem. Commun. 2015, 54(259), 7256. doi: 10.1039/C8CC90288G
[17]	Wang, W. F.; Hanindita, F.; Tanaka, Y.; Ochiai, K.; Sato, H.; Li, Y. X.; Yasuda, T.; Ito, S. Angew. Chem. Int. Ed. 2023, 62(8), e202218176. doi: 10.1002/anie.v62.8
[18]	Wang, W. F.; Hanindita, F.; Webster, R. D.; Ito, S. CCS Chem. 2022, 1.
[19]	Wang, W. F.; Hanindita, F.; Hamamoto, Y.; Li, Y. X.; Ito, S. Nat. Commun. 2022, 13(1), 1498. doi: 10.1038/s41467-022-29106-w
[20]	Guo, X. Y.; Yuan, Z. Y.; Zhu, Y. P.; Li, Z. H.; Huang, R. K.; Xia, Z. M.; Zhang, W. X.; Li, Y.; Wang, J. B. Angew. Chem. Int. Ed. 2019, 58(47), 16966. doi: 10.1002/anie.v58.47
[21]	Miao, D.; Aumaitre, C.; Morin, J-F. J. Mater. Chem. C 2019, 7(10), 3015. doi: 10.1039/C8TC05288C
[22]	Miao, D.; Michele, V. D.; Gagnon, F.; Aumaître, C.; Lucotti, A.; Zoppo, M. D.; Lirette, F.; Tommasini, M.; Morin, J-F. J. Am. Chem. Soc. 2021, 143(30), 11302. doi: 10.1021/jacs.1c05616
[23]	Hager, J.; Kang, S.; Chmielewski, P. J.; Lis, T.; Kim, D.; Stępień, M. Org. Chem. Front. 2022, 9(12), 3179. doi: 10.1039/D2QO00421F
[24]	Hu, Y. C.; Jia, Y. Y.; Tuo, Z. K.; Zhou, W. Org. Lett. 2023, 25(11), 1845. doi: 10.1021/acs.orglett.3c00321
[25]	Hou, D. F.; Balli, H. Helv. Chim. Acta 1992, 75(8), 2608. doi: 10.1002/hlca.v75:8
[26]	(a) Rubio-Presa, R.; Pedrosa, M. R.; Fernández-Rodríguez, M. A.; Arnáiz, F. J.; Sanz, R. Org. Lett. 2017, 19(19), 5470. doi: 10.1021/acs.orglett.7b02792 pmid: 28952319
	(b) Hernández-Ruiz, R.; Rubio-Presa, R.; Suárez-Pantiga, S.; Pedrosa, M. R.; Fernández-Rodríguez, M. A.; Tapia, M. J.; Sanz, R. Chem. Eur. J. 2021, 27(54), 13613. doi: 10.1002/chem.v27.54 pmid: 28952319
[27]	Boldt, S.; Parpart, S.; Villinger, A.; Ehlers, P.; Langer P. Chem. Int. Ed. 2017, 56(16), 4575. doi: 10.1002/anie.v56.16
[28]	Pierrat, P.; Hesse, S.; Cebrián, C.; Gros, P. C. Org. Biomol. Chem. 2017, 15(40), 8568. doi: 10.1039/C7OB02149F
[29]	Parpart, S.; Boldt, S.; Ehlers, P.; Langer, P. Org. Lett. 2018, 20(1), 122. doi: 10.1021/acs.orglett.7b03477 pmid: 29232149
[30]	Ibrahim, D.; Boulet, P.; Gros, P. C.; Pierrat, P. Eur. J. Org. Chem. 2021, 2021(22), 3331. doi: 10.1002/ejoc.v2021.22
[31]	Ge, Q. M.; Li, B.; Wang, B. Q. Org. Biomol. Chem. 2016, 14(5), 1814. doi: 10.1039/C5OB02515J
[32]	Li, Q-Q.; Ochiai, K.; Lee, C-A.; Ito, S. Org. Lett. 2020, 22(15), 6132. doi: 10.1021/acs.orglett.0c02203
[33]	Ghorai, D.; Choudhury, J. ACS Catal. 2015, 5(4), 2692. doi: 10.1021/acscatal.5b00243
[34]	Li, Q-Q.; Hamamoto, Y.; Tan, C. C. H.; Sato, H.; Ito, S. Org. Chem. Front. 2022, 9(15), 4128. doi: 10.1039/D2QO00941B
[35]	Davies, D. L.; Ellul, C. E.; Macgregor, S. A.; McMullin, C. L.; Singh, K. J. Am. Chem. Soc. 2015, 137(30), 9659. doi: 10.1021/jacs.5b04858 pmid: 26115418
[36]	Villar, J. M.; Suárez, J.; Varela, J. A.; Saá, C. Org. Lett. 2017, 19(7), 1702. doi: 10.1021/acs.orglett.7b00478 pmid: 28301167
[37]	Wang, T. B.; Zheng, Q. Z.; Wang, L. H.; Huang, Z. M.; Zhang, H. X.; Zhang, Y. M.; Zhang, C.; Gao, G. Chem. Commun. 2022, 58(4), 541. doi: 10.1039/D1CC06194A
[38]	(a) Mellerup, S. K.; Wang, S. N. Trends Chem. 2019, 1(1), 77. doi: 10.1016/j.trechm.2019.01.003
	(b) Sun, W. T.; Guo, J. X.; Fan, Z. M.; Yuan, L. Z.; Ye, K. Q.; Dou, C. D.; Wang, Y. Angew. Chem. Int. Ed. 2022, 61(40), e202209271. doi: 10.1002/anie.v61.40
	(c) Zhao, R. Y.; Liu, J.; Wang, L. X. Acc. Chem. Res. 2020, 53(8), 1557. doi: 10.1021/acs.accounts.0c00281
[39]	(a) Xu, X. Y.; Liu, M. Y.; Li, C. L.; Liu, X. G. Chin. J. Org. Chem. 2023, 43(5), 1611. doi: 10.6023/cjoc202212038
	(b) Wang, J-Y.; Pei, J. Chin. Chem. Lett. 2016, 27(8), 1139. doi: 10.1016/j.cclet.2016.06.014
	(c) Campbell, P. G.; Marwitz, A. J. V.; Liu, S-Y. Angew. Chem. Int. Ed. 2012, 51(18), 6074. doi: 10.1002/anie.v51.25
[40]	Li, C. L.; Liu, Y. M.; Sun, Z.; Zhang, J. Y.; Liu, M. Y.; Zhang, C.; Zhang, Q.; Wang, H. J.; Liu, X. G. Org. Lett. 2018, 20(10), 2806. doi: 10.1021/acs.orglett.8b00554
[41]	Guo, Y. K.; Zhang, L.; Li, C. L.; Jin, M. J.; Zhang, Y. L.; Ye, J. C.; Chen, Y.; Wu, X. M.; Liu, X. G. J. Org. Chem. 2021, 86(18), 12507. doi: 10.1021/acs.joc.1c00777