Citation:
Danqing Wu, Jiajun Liu, Tianyu Li, Dazhen Xu, Zhiwei Miao. Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways[J]. University Chemistry,
;2024, 39(11): 146-157.
doi:
10.12461/PKU.DXHX202403087
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The 1,2-difunctionalization of olefins via radical pathways is a crucial method in organic synthesis for the direct formation of C—X (X = C, N, O, etc.) bonds from olefins. This approach offers several advantages, including high regioselectivity, step economy, and atom economy, making it compatible with the principles of green chemistry. The development of simple and efficient methods for constructing carbon-oxygen bonds is a significant area of interest in organic chemistry due to the prevalence of organic functional compounds containing these bonds. This review summarizes the recent progress in constructing carbon-oxygen bonds concurrently with carbon-carbon, carbon-nitrogen, carbon-sulfur, and carbon-halogen bonds. Additionally, the article discusses the future directions for research in this field.
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-
-
[1]
Huang, H. M.; Xie, Y. J.; Hu, J. H.; Xie, P.; Qian, B. J. Am. Chem. Soc. 2013, 135, 18327.
-
[2]
Dagousset, G.; Barthelemy, A. L.; Tuccio, B.; Magnier, E. Angew. Chem. Int. Ed. 2018, 57, 13790.
-
[3]
Shi, X. D.; Zhang, S. Y.; Wang, C. H.; Ye, X. H. Angew. Chem. Int. Ed. 2020, 59, 20470.
-
[4]
Shenvi, R. A.; Crossley, S. W. M.; Obradors, C.; Martinez, R. M. Chem. Rev. 2016, 116, 8912.
-
[5]
Zhu, S. Q.; Tu, H. Y.; Qing, F. L.; Chu, L. L. Synthesis 2020, 52, 1346.
-
[6]
Hemric, B. N. Org. Biomol. Chem. 2021, 19, 46.
-
[7]
Vessally, E.; Ebadi, A.; Hossaini, Z.; Heravi, M. R. P.; Azizi, B. RSC Adv. 2021, 11, 13138.
-
[8]
Sodeoka, M.; Egami, H. Angew. Chem. Int. Ed. 2014, 53, 8294.
-
[9]
Sigman, M. S.; Jensen, K. H. Org. Biomol. Chem. 2008, 6, 4083.
-
[10]
Chen, Q. Y.; Guo, Y.; Zhao, Z. G.; Li, L.; Huang, M. W.; Liu, C.; Xiao, J. C. Org. Lett. 2015, 17, 4714.
-
[11]
Muñiz, K. Chem. Soc. Rev. 2004, 33, 166.
-
[12]
Sigman, M. S.; Jensen, K. H. Org. Biomol. Chem. 2008, 6, 4083.
-
[13]
Lei, A. W.; Huang, Z. L.; Jin, L. Q.; Feng, Y.; Peng, Pan.; Yi. H. Angew. Chem. Int. Ed. 2013, 52, 7151.
-
[14]
Li, J. H.; Song, L. J.; Jiang, S. S.; Gu, C. C.; Li, Y.; Dong, Y. X. Org. Lett. 2018, 20, 7594.
-
[15]
Mandal, S. K.; Swain, A. K.; Ahmed, J.; Govindarajan, R. J. Org. Chem. 2019, 84, 13490.
-
[16]
Li, S. H.; Li, Q. K.; Huang, R.; Meng, B. Y.; Peng, D. Q.; Wang, S. H.; Liu, S. H.; Fan, W. ACS. Catal. 2020, 10, 4012.
-
[17]
Jin, C.; Yu, C. M.; Yan, Z. Y.; Huang, P. Y.; Shi, X. Y.; Zhuang, X. H.; Zhu, R.; Sun, B. Org. Lett. 2021, 23, 617.
-
[18]
Chemler, S. R.; Kim, J. W.; Fuller, P. H. J. Am. Chem. Soc. 2008, 130, 17638.
-
[19]
Zhang, W. B.; Yang, G. Q.; Zhang, X. H.; Wu, L.; Li, Y.; Kou, X. Z. Org. Lett. 2015, 17, 5566.
-
[20]
Wang, Q.; Chen, A. W.; Hemric, B. N. ACS Catal. 2019, 9, 10070.
-
[21]
Huang, J. M.; Wan, J. L. Org. Lett. 2022, 24, 8914.
-
[22]
Han, J. L.; Wang, Y.; Deng, L. L.; Mei, H. B.; Du, B. N.; Pan, Y. Green Chem. 2018, 20, 3444.
-
[23]
Sun, J. W.; Ma, D. K.; Yan, J. Y.; Zhang, Z. F. Chin. Chem. Lett. 2019, 30, 1509.
-
[24]
Gao, B.; Liu, X. J.; Yan, Q.; Yang, R. T.; Jiang, T.; Zhang, X. L. Synthesis 2022, 54, 2258.
-
[25]
Liu, C. J.; Xia, Y.; Jin, W. W.; Zhang, Y. H.; Wang, B.; Liu, T. X.; Xue, F.; Chen, Z. R. Green Chem. 2022, 24, 3250.
-
[26]
Majee, A.; Zyryanov, G. V.; Hajra, A.; Kundu, S. K.; Santra, S.; Chakraborty, N. RSC Adv. 2015, 5, 56780.
-
[27]
Li, J. H.; Song, R. J.; Wan, C. Org. Lett. 2019, 21, 2800.
-
[28]
Li, J. H.; Song, R. J.; Zhang, T. T.; Luo, M. J.; Li, Y. Org. Lett. 2020, 22, 7250.
-
[29]
Li, H. L.; Li, Z.Q.; Zhai, L. L.; Fang, B. W. Tetrahedron Letters. 2023, 126, 154647.
-
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