银催化环丙烯酮与醇的C—C键断裂加成反应
收稿日期: 2024-03-05
修回日期: 2024-03-20
网络出版日期: 2024-04-25
基金资助
国家自然科学基金(21702160); 大连理工大学精细化工国家重点实验室(KF2311)
Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C—C Bond Cleavage
Received date: 2024-03-05
Revised date: 2024-03-20
Online published: 2024-04-25
Supported by
National Natural Science Foundation of China(21702160); State Key Laboratory of Fine Chemicals, Dalian University of Technology(KF2311)
张书林 , 张周 , 孙萌 . 银催化环丙烯酮与醇的C—C键断裂加成反应[J]. 有机化学, 2024 , 44(7) : 2233 -2240 . DOI: 10.6023/cjoc202403007
An efficient method for the synthesis of α-phenylcinnamates via silver catalyzed C—C bond activation reaction of cyclopropenone and alcohol was developed. This protocol features a simple reaction system, specific regioselectivity, good functional group compatibility and good yields. It is of great significance for the later modification of natural products.
| [1] | (a) Clifford, M. N. J. Sci. Food Agric. 2000, 80, 1033. |
| [1] | (b) Shuab, R.; Lone, R.; Koul, K. K. Acta Physiol. Plant. 2016, 38, 1. |
| [2] | Xu, H.-T.; Zhang, C.-G.; He, Y.-Q.; Shi, S.-S.; Wang, Y.-L.; Chou, G.-X. Phytochemistry 2019, 164, 111. |
| [3] | Zhang, J.-L.; Cui, M.; He, Y.; Yu, H.-L.; Guo, D.-A. J. Pharm. Biomed. Anal. 2005, 36, 1029. |
| [4] | Hu, Z.; Silipo, A.; Li, W.; Molinaro, A.; Yu, B. J. Org. Chem. 2019, 84, 13733. |
| [5] | (a) To, C. T.; Chan, K. S. Acc. Chem. Res. 2017, 50, 1702. |
| [5] | (b) Kim, D.-S.; Park, W.-J.; Jun, C.-H. Chem. Rev. 2017, 117, 8977. |
| [5] | (c) Fumagalli, G.; Stanton, S.; Bower, J. F. Chem. Rev. 2017, 117, 9404. |
| [5] | (d) Deng, L.; Dong, G. Trends Chem. 2020, 2, 183. |
| [6] | (a) Breslow, R.; Haynie, R.; Mirra, J. J. Am. Chem. Soc. 1959, 81, 247. |
| [6] | (b) Vol’pin, M. E.; Koreshkov, Y. D.; Kursanov, D. N. Izv. Akad. Nauk SSSR, Ser. Khim. 1959, 8, 535. |
| [7] | (a) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. |
| [7] | (b) Komatsu, K.; Kitagawa, T. Chem. Rev. 2003, 103, 1371. |
| [7] | (c) Prasad Raiguru, B.; Nayak, S.; Ranjan Mishra, D.; Das, T.; Mohapatra, S.; Priyadarsini Mishra, N. Asian J. Org. Chem. 2020, 9, 1088. |
| [8] | (a) Xie, F.; Yu, S.; Qi, Z.; Li, X. Angew. Chem., Int. Ed. 2016, 55, 15351. |
| [8] | (b) Yu, S.; Li, X. Org. Lett. 2014, 16, 1220. |
| [8] | (c) Liu, B.; Yang, L.; Dong, Z.; Chang, J.; Li, X. Org. Lett. 2021, 23, 7199. |
| [8] | (d) Yuan, T.; Pi, C.; You, C.; Cui, X.; Du, S.; Wan, T.; Wu, Y. Chem. Commun. 2019, 55, 163. |
| [8] | (e) Shi, Y.; Xing, H.; Huang, T.; Liu, X.; Chen, J.; Guo, X.; Li, G.-B.; Wu, Y. Chem. Commun. 2020, 56, 1585. |
| [8] | (f) Shi, Y.; Huang, T.; Wang, T.; Chen, J.; Liu, X.; Wu, Z.; Huang, X.; Zheng, Y.; Yang, Z.; Wu, Y. Chem.-Eur. J. 2021, 27, 13346. |
| [8] | (g) Liu, Y.; Tian, Y.; Su, K.; Wang, P.; Guo, X.; Chen, B. Org. Chem. Front. 2019, 6, 3973. |
| [8] | (h) Miao, W.-H.; Gao, W.-X.; Huang, X.-B.; Liu, M.-C.; Zhou, Y.-B.; Wu, H.-Y. Org. Lett. 2021, 23, 9425. |
| [8] | (i) Tong, Q.; Xiu, R.-F.; Chen, J.-H.; Zhang, Y.; Cui, B.-D.; Wan, N.-W.; Chen, Y.-Z.; Han, W.-Y. ACS Catal. 2023, 13, 12692. |
| [9] | Klimova, E. I.; Berestneva, T. K.; Ramirez, L. R.; Cinquantini, A.; Corsini, M.; Zanello, P.; Hernandez-Ortega, S.; Garcia, M. M. Eur. J. Org. Chem. 2003, 2003, 4265. |
| [10] | (a) Ren, J.-T.; Wang, J.-X.; Tian, H.; Xu, J.-L.; Hu, H.; Aslam, M.; Sun, M. Org. Lett. 2018, 20, 6636. |
| [10] | (b) Xu, J.-L.; Tian, H.; Kang, J.-H.; Kang, W.-X.; Sun, W.; Sun, R.; Li, Y.-M.; Sun, M. Org. Lett. 2020, 22, 6739. |
| [10] | (c) Zhang, Y.-B.; Li, B.-S.; Xu, G.-J.; Sun, W.; Sun, M. Org. Lett. 2023, 25, 3922. |
| [10] | (d) Hu, H.; Li, B.-S.; Xu, J.-L.; Sun, W.; Wang, Y.; Sun, M. Chem. Commun. 2022, 58, 4743. |
| [11] | (a) Nanda, T.; Ravikumar, P. C. Org. Lett. 2020, 22, 1368. |
| [11] | (b) Nanda, T.; Biswal, P.; Pati, B. V.; Banjare, S. K.; Ravikumar, P. C. J. Org. Chem. 2021, 86, 2682. |
| [12] | Greco, R.; Tiburcio, E.; Lucas, B. P.; Ferrando-Soria, J.; Armentano, D.; Pardo, E.; Leyva-Perez, A. Mol. Catal. 2022, 522, 112228. |
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