芳酮类化合物的合成研究进展

doi:10.6023/cjoc202104049

摘要/Abstract

芳酮类化合物具有多种生物活性, 同时也是重要的精细化工品, 因此其合成方法受到了广泛关注. 对近五至八年来芳酮类化合物的合成方法进行总结, 通过对其反应机理进行探讨, 将这些反应大致分为三类, 即通过过渡金属催化机理的偶联反应、通过自由基机理的反应及通过其他机理的反应, 期望为芳酮类化合物的合成新方法提供启发.

关键词: 芳甲酰基, 反应机理, 合成方法

Aroyl compounds exhibit various biological activities and are important fine chemicals as well. Therefore, their synthetic methods have attracted considerable attention. It is the first time to summarize the synthetic methods of aroyl compounds in the past five to eight years. These reactions can be classified into three parts by their reaction mechanism, namely, coupling reaction catalyzed transition metals, the free radical mechanism and aromylation reactions carried out by other mechanisms. It is expected that inspiration of new synthetic methods will be provided for the synthesis of compounds bear aroyl group in this review.

Key words: aroyl group, reaction mechanism, synthetic method

引用此文

刘亮, 刘文波, 崔冬梅, 曾明. 芳酮类化合物的合成研究进展[J]. 有机化学, 2021, 41(11): 4289-4305.

Liang Liu, Wenbo Liu, Dong-Mei Cui, Ming Zeng. Progress in the Synthesis of Aroyl Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4289-4305.

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

分享此文

图/表 23

图式1. 合成3-芳甲酰基吲哚可能的反应机理

Scheme 1. Possible reaction mechanism for the synthesis of 3-Aroyl indole

图式2. 可能的反应机理

Scheme 2. Possible reaction mechanism

图式3. 合成二芳基甲酮可能的反应机理

Scheme 3. Possible reaction mechanism for the synthesis of diaryl ketone

图式4. 合成二甲氨基吡啶盐可能的反应机理

Scheme 4. Possible reaction mechanism for the synthesis of dimethylaminopyridinium salts

图式5. 合成芳基酰胺可能的反应机理

Scheme 5. Possible reaction mechanism for the synthesis of arylamide

图式6. 合成芳甲酰基吡咯酮可能的反应机理

Scheme 6. Possible reaction mechanism for synthesis of aroyl pyrrolidone

图式7. 合成3-芳甲酰基吡啶并吡咯可能的反应机理

Scheme 7. Possible reaction mechanism for the synthesis of 3- aroylpyridopyrroles

图式8. 合成2-芳甲酰基苯并呋喃可能的反应机理

Scheme 8. Possible reaction mechanism for the synthesis of 2-aroyl benzofurans

图式9. 2-芳基吡啶的芳甲酰基化反应可能的反应机理

Scheme 9. Possible reaction mechanism of the aromatic acylation of 2-arylpyridine

图式10. 铑催化合成芳基甲醛可能的反应机理

Scheme 10. Possible reaction mechanism for rhodium catalyzed synthesis of aryl formaldehyde

图式11. 铜催化合成2-芳甲酰基取代的三嗪并咪唑可能的反应机理

Scheme 11. Possible mechanism for copper catalyzed synthesis of 2-aroyl substituted triazinoimidazoles

图式12. 钯催化2-芳基吡啶的芳甲酰基化反应可能的反应机理

Scheme 12. Possible reaction mechanism for palladium catalyzed aromatic acylation of 2-arylpyridine

图式13. 钯催化2-芳甲酰基取代苯并噻唑可能的反应机理

Scheme 13. Possible reaction mechanism for palladium catalyzed synthesis of 2-aroyl substituted benzothiazole derivatives

图式14. 光催化α,β-不饱和酮的芳甲酰基化反应可能的反应机理

Scheme 14. Possible mechanism for photocatalytic aromatic acylation of α,β-unsaturated ketones

图式15. 光催化α,β-不饱和酮和芳甲酰氯的芳甲酰基化反应可能的反应机理

Scheme 15. Possible reaction mechanism for photocatalytic aromatic acylation of α,β-unsaturated ketones with aroyl chloride

图式16. 光催化烯烃和芳甲酰氯的芳甲酰基化反应可能的反应机理

Scheme 16. Possible reaction mechanism for photocatalytic aromatic acylation of alkenes with aroyl chloride

图式17. 光催化芳甲酰基氟作为酰基化试剂可能的反应机理

Scheme 17. Possible reaction mechanism for photocatalytic aroyl fluoride as acylation reagent

图式18. 光催化合成苯并吡咯酮可能的机理

Scheme 18. Possible mechanism for the photocatalytic synthesis of benzopyrrolone

图式19. 光催化促进的胺(Sp3-H)的芳甲酰基化反应可能的机理

Scheme 19. Possible mechanism for photocatalysis promotes the arylformylation of amines

图式20. 可见光催化条件下芳基酮酸作为芳甲酰基化试剂

Scheme 20. Aryl keto acid as aroformylation reagent under visible light catalysis

图式21. 香豆素的芳甲酰基化反应可能的机理

Scheme 21. Possible mechanism for aromatic acylation of coumarin

图式22. [2+2]偶联和[4+1]反应合成2-芳甲酰基苯并呋喃可能的反应机理

Scheme 22. Possible mechanism for the synthesis of 2-aroyl benzofuran via [2+2] coupling and [4+1] cyclization

图式23. 通过亚甲基氧化合成芳甲酰基化合物可能的反应机理

Scheme 23. Possible reaction mechanism for synthesis of aroyl compounds by methylene oxidation

参考文献 87

[1]	Zhu, X.-L.; Tian, X.-Q.; Xu, H.-H.; Wang, H.-M.; Chen, Q.-H.; Zeng, X.-H. Bioorg. Med. Chem. Lett. 2020, 30, 127554. doi: 10.1016/j.bmcl.2020.127554
[2]	Duan, J. X.; Cai, X.; Meng, F.; Lan, L.; Hart, C.; Matteucci, M. J. Med. Chem. 2007, 50, 1001. doi: 10.1021/jm061348t
[3]	Mai, A.; Massa, S.; Ragno, R.; Cerbara, I.; Jesacher, F.; Loidl, P.; Brosch, G. J. Med. Chem. 2003, 46, 512. doi: 10.1021/jm021070e
[4]	Han, Y.; Tian, Y.; Wang, R.; Fu, S.; Jiang, J.; Dong, J.; Qin, M.; Hou, Y.; Zhao, Y. Bioorg. Chem. 2020, 104, 104197. doi: 10.1016/j.bioorg.2020.104197
[5]	Turan-Zitouni, G.; Yurttaş, L.; Kaplancıklı, Z. A.; Can, Ö. D.; Demir Özkay, Ü. Med. Chem. Res. 2015, 24, 2406. doi: 10.1007/s00044-014-1309-1
[6]	Patch, R. J.; Brandt, B. M.; Asgari, D.; Baindur, N.; Chadha, N. K.; Georgiadis, T.; Cheung, W. S.; Petrounia, I. P.; Donatelli, R. R.; Chaikin, M. A.; Player, M. R. Bioorg. Med. Chem. Lett. 2007, 17, 6070. doi: 10.1016/j.bmcl.2007.09.057
[7]	Wang, L.; Guo, D.-G.; Wang, Y.-Y.; Zheng, C.-Z. RSC Adv. 2014, 4, 58895. doi: 10.1039/C4RA11747F
[8]	Rane, R. A.; Telvekar, V. N. Bioorg. Med. Chem. Lett. 2010, 20, 5681. doi: 10.1016/j.bmcl.2010.08.026
[9]	Çınarlı, M.; Yüksektepe Ataol, Ç.; Çınarlı, E.; İdil, Ö. J. Mol. Struct. 2020, 1213, 128152. doi: 10.1016/j.molstruc.2020.128152
[10]	Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030. doi: 10.1039/c1cs15093f pmid: 21792454
[11]	Bode, K.-D.; Dieterich, D.; Eistert, B.; Gipp, R.; Henecka, H.; Herlinger, H.; Jira, R.; Kramer, D.; Kabbe, H.-J.; Lüttringhaus, A.; Regitz, M.; Schellhammer, C.-W.; Söll, H.; Stetter, H.; Wilms, H.; Wingler, F. Methoden der Organischen Chemie (Houben-Weyl), Thieme, Stuttgart, 1973, p. 268.
[12]	Zhao, W.; Liu, W. Chin. J. Org. Chem. 2015, 35, 55. (in Chinese)
	(赵蔚, 刘伟, 有机化学, 2015, 35, 55.) doi: 10.6023/cjoc201407032
[13]	Molle, G.; Bauer, P. J. Am. Chem. Soc. 1982, 104, 3481. doi: 10.1021/ja00376a039
[14]	Bosque, I.; Chinchilla, R.; Gonzalez-Gomez, J. C.; Guijarro, D.; Alonso, F. Org. Chem. Front. 2020, 7, 1717. doi: 10.1039/D0QO00587H
[15]	Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114. doi: 10.1002/anie.v48:23
[16]	Swain, C. G. J. Am. Chem. Soc. 1947, 69, 2306. doi: 10.1021/ja01202a018
[17]	Arthuis, M.; Pontikis, R.; Florent, J.-C. Org. Lett. 2009, 11, 4608. doi: 10.1021/ol901875z pmid: 19764711
[18]	Zhao, M.-N.; Ran, L.; Chen, M.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. ACS Catal. 2015, 5, 1210. doi: 10.1021/cs5019106
[19]	Tjutrins, J.; Arndtsen, B. A. J. Am. Chem. Soc. 2015, 137, 12050. doi: 10.1021/jacs.5b07098
[20]	Lian, Z.; Friis, S. D.; Skrydstrup, T. Chem. Commun. 2015, 51, 1870. doi: 10.1039/C4CC09303H
[21]	Garrison Kinney, R.; Tjutrins, J.; Torres, G. M.; Liu, N. J.; Kulkarni, O.; Arndtsen, B. A. Nat. Chem. 2018, 10, 193. doi: 10.1038/nchem.2903 pmid: 29359763
[22]	Levesque, T. M.; Kinney, R. G.; Arndtsen, B. A. Chem. Sci. 2020, 11, 3104. doi: 10.1039/d0sc00085j pmid: 34122815
[23]	Quesnel, J. S.; Fabrikant, A.; Arndtsen, B. A. Chem. Sci. 2016, 7, 295. doi: 10.1039/C5SC02949J
[24]	Lagueux-Tremblay, P.-L.; Fabrikant, A.; Arndtsen, B. A. ACS Catal. 2018, 8, 5350. doi: 10.1021/acscatal.8b00757
[25]	Odell, L. R.; Russo, F.; Larhed, M. Synlett 2012, 23, 685. doi: 10.1055/s-0031-1290350
[26]	Ningegowda, R.; Bhaskaran, S.; Sajith, A. M.; Aswathanarayanappa, C.; Padusha, M. S. A.; Shivananju, N. S.; Priya, B. S. Aust. J. Chem. 2017, 70, 44. doi: 10.1071/CH16213
[27]	Darbem, M. P.; Kanno, K. S.; de Oliveira, I. M.; Esteves, C. H. A.; Pimenta, D. C.; Stefani, H. A. New. J. Chem. 2019, 43, 696. doi: 10.1039/C8NJ04540B
[28]	Dong, Y.; Sun, S.; Yang, F.; Zhu, Y.; Zhu, W.; Qiao, H.; Wu, Y.; Wu, Y. Org. Chem. Front. 2016, 3, 720. doi: 10.1039/C6QO00075D
[29]	Jafarpour, F.; Rashidi-Ranjbar, P.; Kashani, A. O. Eur. J. Org. Chem. 2011, 2011, 2128. doi: 10.1002/ejoc.201001733
[30]	Sun, N.; Sun, Q.; Zhao, W.; Jin, L.; Hu, B.; Shen, Z.; Hu, X. Adv. Synth. Catal. 2019, 361, 2117. doi: 10.1002/adsc.v361.9
[31]	Ismael, A.; Gevorgyan, A.; Skrydstrup, T.; Bayer, A. Org. Process Res. Dev. 2020, 24, 2665. doi: 10.1021/acs.oprd.0c00325
[32]	Ryotaro, N.; Hideki, Y.; Koichiro, O. Chem. Lett. 2011, 40, 904. doi: 10.1246/cl.2011.904
[33]	Roy, T.; Rydfjord, J.; Sävmarker, J.; Nordeman, P. Tetrahedron Lett. 2018, 59, 1230. doi: 10.1016/j.tetlet.2018.02.035
[34]	Wang, Z.; Yin, Z.; Wu, X.-F. Chem.-Eur. J. 2017, 23, 15026. doi: 10.1002/chem.201703994
[35]	Peng, J.-B.; Geng, H.-Q.; Li, D.; Qi, X.; Ying, J.; Wu, X.-F. Org. Lett. 2018, 20, 4988. doi: 10.1021/acs.orglett.8b02109
[36]	Ying, J.; Le, Z.; Wu, X.-F. Org. Chem. Front. 2020, 7, 2757. doi: 10.1039/D0QO00874E
[37]	Ying, J.; Le, Z.; Bao, Z.-P.; Wu, X.-F. Org. Chem. Front. 2020, 7, 1006. doi: 10.1039/D0QO00007H
[38]	Scheffold, R.; Orlinski, R. J. Am. Chem. Soc. 1983, 105, 7200. doi: 10.1021/ja00362a047
[39]	Arisawa, M.; Tanii, S.; Yamaguchi, M. Chem. Commun. 2014, 50, 15267. doi: 10.1039/C4CC07759H
[40]	Zhang, Y.; Chen, J. L.; Chen, Z. B.; Zhu, Y. M.; Ji, S. J. J. Org. Chem. 2015, 80, 10643. doi: 10.1021/acs.joc.5b01758 pmid: 26452462
[41]	Ying, J.; Fu, L.-Y.; Zhou, C.; Qi, X.; Peng, J.-B.; Wu, X.-F. Eur. J. Org. Chem. 2018, 2018, 2780. doi: 10.1002/ejoc.201800471
[42]	Wang, Y.; Zhou, Y.; Lei, M.; Hou, J.; Jin, Q.; Guo, D.; Wu, W. Tetrahedron 2019, 75, 1180. doi: 10.1016/j.tet.2019.01.023
[43]	Geng, H.-Q.; Wang, L.-C.; Hou, C.-Y.; Wu, X.-F. Org. Lett. 2020, 22, 1160. doi: 10.1021/acs.orglett.0c00015
[44]	Higashi, S.; Uno, S.; Ohsuga, Y.; Noumi, M.; Saito, R. Tetrahedron Lett. 2020, 61, 152466. doi: 10.1016/j.tetlet.2020.152466
[45]	Li, Y.; Xiong, W.; Zhang, Z.; Xu, T. J. Org. Chem. 2020, 85, 6392. doi: 10.1021/acs.joc.0c00161
[46]	Weng, Y.; Yang, T.; Chen, H.; Chen, Z.; Zhu, M.; Zhan, X. ChemistrySelect 2019, 4, 14233. doi: 10.1002/slct.v4.48
[47]	Gong, J.; Hu, K.; Shao, Y.; Li, R.; Zhang, Y.; Hu, M.; Chen, J. Org. Biomol. Chem. 2020, 18, 488. doi: 10.1039/C9OB02408E
[48]	Tlili, A.; Schranck, J.; Pospech, J.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 6293. doi: 10.1002/anie.201301663
[49]	Li, W.; Zhang, S.; Feng, X.; Yu, X.; Yamamoto, Y.; Bao, M. Org. Lett. 2021, 23, 2521. doi: 10.1021/acs.orglett.1c00464
[50]	Luo, L.; Zhou, Z.; Zhu, J.; Lu, X.; Wang, H. Tetrahedron Lett. 2016, 57, 4987.
[51]	Chatupheeraphat, A.; Liao, H.-H.; Srimontree, W.; Guo, L.; Minenkov, Y.; Poater, A.; Cavallo, L.; Rueping, M. J. Am. Chem. Soc. 2018, 140, 3724. doi: 10.1021/jacs.7b12865 pmid: 29461813
[52]	Liu, Z.; Wang, P.; Yan, Z.; Chen, S.; Mu, T. Beilstein J. Org. Chem. 2020, 16, 645. doi: 10.3762/bjoc.16.61
[53]	Zhang, Q.; Li, J.; Li, J.; Yuan, S.; Li, D. Tetrahedron Lett. 2020, 61, 152399. doi: 10.1016/j.tetlet.2020.152399
[54]	Monir, K.; Kumarbagdi, A.; Mishra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2014, 356, 1105. doi: 10.1002/adsc.v356.5
[55]	Kaswan, P.; Pericherla, K.; Saini, H. K.; Kumar, A. RSC Adv. 2015, 5, 3670. doi: 10.1039/C4RA13056A
[56]	Li, J. J.; Song, C.; Cui, D.-M.; Zhang, C. Org. Biomol. Chem. 2017, 15, 5564. doi: 10.1039/C7OB01018D
[57]	Behera, A.; Ali, W.; Guin, S.; Khatun, N.; Mohanta, P. R.; Patel, B. K. RSC Adv. 2015, 5, 33334. doi: 10.1039/C5RA03836G
[58]	Pipaliya, B. V.; Chakraborti, A. K. J. Org. Chem. 2017, 82, 3767. doi: 10.1021/acs.joc.7b00226 pmid: 28299930
[59]	Zhao, B.; Shang, R.; Cheng, W.-M.; Fu, Y. Org. Chem. Front. 2018, 5, 1782. doi: 10.1039/C8QO00253C
[60]	Cao, H.; Pu, W.; Zhang, J.; Yan, P.; Zhang, J.; Xu, S. Synlett 2020, 31, 1287. doi: 10.1055/s-0040-1707140
[61]	Khatun, N.; Banerjee, A.; Santra, S. K.; Behera, A.; Patel, B. K. RSC Adv. 2014, 4, 54532. doi: 10.1039/C4RA11014E
[62]	Joe, C. L.; Doyle, A. G. Angew. Chem., Int. Ed. 2016, 55, 4040. doi: 10.1002/anie.201511438
[63]	Wang, H.; Zhou, S.-L.; Guo, L.-N.; Duan, X.-H. Tetrahedron 2015, 71, 630. doi: 10.1016/j.tet.2014.12.029
[64]	Yuan, J.-W.; Yin, Q.-Y.; Yang, L.-R.; Mai, W.-P.; Mao, P.; Xiao, Y.-M.; Qu, L.-B. RSC Adv. 2015, 5, 88258. doi: 10.1039/C5RA16573C
[65]	Pimpasri, C.; Sumunnee, L.; Yotphan, S. Org. Biomol. Chem. 2017, 15, 4320. doi: 10.1039/C7OB00776K
[66]	Wang, G.-Z.; Shang, R.; Cheng, W.-M.; Fu, Y. Org. Lett. 2015, 17, 4830. doi: 10.1021/acs.orglett.5b02392
[67]	Wang, C.-M.; Song, D.; Xia, P.-J.; Wang, J.; Xiang, H.-Y.; Yang, H. Chem.-Asian J. 2018, 13, 271. doi: 10.1002/asia.201701738
[68]	Lei, Z.; Banerjee, A.; Kusevska, E.; Rizzo, E.; Liu, P.; Ngai, M. Y. Angew. Chem., Int. Ed. 2019, 58, 7318. doi: 10.1002/anie.v58.22
[69]	Meng, Q. Y.; Döben, N.; Studer, A. Angew. Chem., Int. Ed. 2020, 59, 19956. doi: 10.1002/anie.v59.45
[70]	Bergonzini, G.; Cassani, C.; Wallentin, C.-J. Angew. Chem., Int. Ed. 2015, 54, 14066. doi: 10.1002/anie.201506432
[71]	Dong, S.; Wu, G.; Yuan, X.; Zou, C.; Ye, J. Org. Chem. Front. 2017, 4, 2230. doi: 10.1039/C7QO00453B
[72]	Xu, S.-M.; Chen, J.-Q.; Liu, D.; Bao, Y.; Liang, Y.-M.; Xu, P.-F. Org. Chem. Front. 2017, 4, 1331. doi: 10.1039/C7QO00012J
[73]	Guo, W.; Lu, L.-Q.; Wang, Y.; Wang, Y.-N.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2015, 54, 2265. doi: 10.1002/anie.201408837
[74]	Majek, M.; Jacobi von Wangelin, A. Angew. Chem., Int. Ed. 2015, 54, 2270. doi: 10.1002/anie.201408516
[75]	Koziakov, D.; Jacobi von Wangelin, A. Org. Biomol. Chem. 2017, 15, 6715. doi: 10.1039/c7ob01572k pmid: 28770941
[76]	Xu, G.-Q.; Xiao, T.-F.; Feng, G.-X.; Liu, C.; Zhang, B.; Xu, P.-F. Org. Lett. 2021. 23, 2846. doi: 10.1021/acs.orglett.1c00226
[77]	Zhu, H.-L.; Zeng, F.-L.; Chen, X.-L.; Sun, K.; Li, H.-C.; Yuan, X.-Y.; Qu, L.-B.; Yu, B. Org. Lett. 2021, 23, 2976. doi: 10.1021/acs.orglett.1c00655
[78]	Zhang, H.; Shi, R.; Ding, A.; Lu, L.; Chen, B.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 12542. doi: 10.1002/anie.201206518
[79]	Jafarpour, F.; Abbasnia, M. J. Org. Chem. 2016, 81, 11982. pmid: 27800677
[80]	Gouthami, P.; Chavan, L. N.; Chegondi, R.; Chandrasekhar, S. J. Org. Chem. 2018, 83, 3325. doi: 10.1021/acs.joc.8b00360
[81]	Pan, Z.; Song, C.; Zhou, W.; Cui, D.-M.; Zhang, C. New. J. Chem 2020, 44, 6182. doi: 10.1039/C9NJ05794C
[82]	Chauhan, J.; Luthra, T.; Sen, S. Eur. J. Org. Chem. 2018, 2018, 4776. doi: 10.1002/ejoc.201800879
[83]	Yamada, Y. M. A.; Arakawa, T.; Hocke, H.; Uozumi, Y. Angew. Chem., Int. Ed. 2007, 46, 704. doi: 10.1002/(ISSN)1521-3773
[84]	Han, L.; Xing, P.; Jiang, B. Org. Lett. 2014, 16, 3428. doi: 10.1021/ol501353q
[85]	Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Ripin, D. H. B. Chem. Rev. 2006, 106, 2943. doi: 10.1021/cr040679f
[86]	Lee, S.; Kim, S. A.; Jang, H.-Y. ACS Omega 2019, 4, 17934. doi: 10.1021/acsomega.9b03064
[87]	Zhao, P.; Yu, X.-X.; Zhou, Y.; Geng, X.; Wang, C.; Huang, C.; Wu, Y.-D.; Zhu, Y.-P.; Wu, A.-X. Org. Lett. 2020, 22, 7103. doi: 10.1021/acs.orglett.0c02415