Recent Advances of the Construction of Trifluoromethylated Quaternary Carbon Center

doi:10.6023/cjoc202001012

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 1901-1911.DOI: 10.6023/cjoc202001012 Previous Articles Next Articles

三氟甲基季碳中心的合成进展

王守锋, 王文贵

济南大学化学化工学院山东省氟化学化工材料重点实验室济南 250022

收稿日期:2020-01-07 修回日期:2020-03-24 发布日期:2020-04-10
通讯作者: 王守锋, 王文贵 E-mail:chm_wangsf@ujn.edu.cn;chm_wangwg@ujn.edu.cn
基金资助:
国家自然科学基金（No.31972850）和山东省重点研发计划（No.2019GSF108223）资助项目.

Recent Advances of the Construction of Trifluoromethylated Quaternary Carbon Center

Wang Shoufeng, Wang Wengui

Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022

Received:2020-01-07 Revised:2020-03-24 Published:2020-04-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31972850) and the Shandong Provincial Key Research Program (No. 2019GSF108223).

Trifluoromethyl is an important group, which is often used in pharmecuticals and agrochemicals. Quaternary carbon centers are widely existed in natural products and synthetic compounds. Recently, the construction of molecules containing trifluoromethylated quaternary carbon centers has been developed rapidly. Starting with direct trifluoromethylation, new synthons and new reactions, the research progress of the synthesis of trifluoromethylated quaternary carbon centers is reviewed.

Key words: trifluoromethyl, quaternary carbon center, research progress

Cite this article

Wang Shoufeng, Wang Wengui. Recent Advances of the Construction of Trifluoromethylated Quaternary Carbon Center[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1901-1911.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] For selected reviews, see:(a) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
(b) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(c) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
(d) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513.
(e) Tian, F.; Yan, G.; Yu, J. Chem. Commun. 2019, 55, 13486.
[2] For selected recent reviews, see:(a) Pierrot, D.; Merk, I. Angew. Chem., Int. Ed. 2020, 59, 36.
(b) Li, C.; Ragab, S.; Liu, G.; Tang, W. Nat. Prod. Rep. 2020, 37, 276.
(c) Feng, J.; Holmes, M.; Krische, M. J. Chem. Rev. 2017, 117, 12564.
(d) Zeng, X.-P.; Cao, Z.-Y.; Wang, Y.-H.; Zhou, F.; Zhou, J. Chem. Rev. 2016, 116, 7330.
(e) Long, R.; Huang, J.; Gong, J.; Yang, Z. Nat. Prod. Rep. 2015, 32, 1584.
[3] Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Soc. Chem. 2012, 134, 10769.
[4] Granados, A.; Rivilla, I.; Cossío, F. P.; Vallribera, A. Chem.-Eur. J. 2019, 25, 8214.
[5] Katayev, D.; Matouśek, V.; Koller, R.; Togni, A. Org. Lett. 2015, 17, 5898.
[6] Calvo, R.; Comas-Vives, A.; Togni, A.; Katayev, D. Angew. Chem., Int. Ed. 2019, 58, 1447.
[7] Früh, N.; Togni, A. Angew. Chem., Int. Ed. 2014, 53, 10813.
[8] Ye, J.-H.; Song, L.; Zhou, W.-J.; Ju, T.; Yin, Z.-B.; Yan, S.-S.; Zhang, Z.; Li, J.; Yu, D.-G. Angew. Chem., Int. Ed. 2016, 55, 10022.
[9] Woźniak, Ł.; Murphy, J. J.; Melchiorre, P. J. Am. Chem. Soc. 2015, 137, 5678.
[10] Matsui, H.; Murase, M.; Yajima, T. Org. Biomol. Chem. 2018, 16, 7120.
[11] Liu, Y.; Zhou, F.; He, K.; Cheng, T.; Zhong, Z.; Liu, Y.; Yang, Y. Phosphorus, Sulfur Silicon Relat. Elem. 2018, 193, 201.
[12] Guo, Y.; Zhao, X.; Zhang, D.; Murahashi, S.-I. Angew. Chem., Int. Ed. 2009, 48, 2047.
[13] Wang, Q.; Huan, F.; Shen, H.; Xiao, J.-C.; Gao, M.; Yang, X.; Murahashi, S.-I.; Chen, Q.-Y.; Guo Y. J. Org. Chem. 2013, 78, 12525.
[14] Foster, R. W.; Lenz, E. N.; Simpkins, N. S.; Stead, D. Chem.-Eur. J. 2017, 23, 8810.
[15] (a) Li, L.; Huang, D.; Chen, Q.-Y.; Guo Y. Synlett 2013, 0611.
(b) Li, L.; Chen, Q.-Y.; Guo, Y. Chem. Commun. 2013, 49, 8764.
[16] Wang, W., Huan, F.; Sun, Y.; Fang, J.; Liu, X.-Y.; Chen, Q.-Y.; Guo, Y. J. Fluorine Chem. 2015, 171, 46.
[17] Tian, P.; Wang, C.-Q.; Cai, S.-H.; Song, S.; Ye, L.; Feng, C.; Loh, T.-P. J. Am. Chem. Soc. 2016, 138, 15869.
[18] Huan, F.; Chen, Q.-Y.; Guo, Y. J. Org. Chem. 2016, 81, 7051.
[19] Wang, W.; Guo, Y.; Sun, K.; Wang, S.; Zhang, S.; Liu, C.; Chen, Q.-Y. J. Org. Chem. 2018, 83, 14588.
[20] Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 4959.
[21] Kawai, H.; Yuan, Z.; Kitayama, T.; Tokunaga, E.; Shibata, N. Angew. Chem., Int. Ed. 2013, 52, 5575.
[22] Kwiatkowski, P.; Cholewiak, A.; Kasztelan, A. Org. Lett. 2014, 16, 5930.
[23] Sanz-Marco, A.; Blay, G.; Vila, C.; Pedro, J. R. Org. Lett. 2016, 18, 3538.
[24] Gao, J.-R.; Wu, H.; Xiang, B.; Yu, W.-B.; Han, L.; Jia, Y.-X. J. Am. Chem. Soc. 2013, 135, 2983.
[25] Ibáñez, I.; Kaneko, M.; Kamei, Y.; Tsutsumi, R.; Yamanaka, M.; Akiyama, T. ACS Catal. 2019, 9, 6903.
[26] Ma, C.-H.; Kang, T.-R.; He, L.; Liu, Q.-Z. Eur. J. Org. Chem. 2014, 3981.
[27] Chen, Q.; Wang, G.; Jiang, X.; Xu, Z.; Lin, L.; Wang, R. Org. Lett. 2014, 16, 1394.
[28] Sim, J.-H.; Park, J-H.; Maity, P.; Song, C.-E. Org. Lett. 2019, 21, 6715.
[29] Hou, X.; Ma, H.; Zhang, Z.; Xie, L.; Qin Z.; Fu, B. Chem. Commun. 2016, 52, 1470.
[30] (a) Hao, X.-Q.; Wang, C.; Liu, S.-L.; Wang, X.; Wang, L.; Gong, J.-F.; Song, M.-P. Org. Chem. Front. 2017, 4, 308.
(b) Lai, X.; Zha, G.; Liu, W.; Xu, Y.; Sun, P.; Xia, T.; Shen, Y. Synlett 2016, 27, 1983
[31] Nikolaev, V. A.; Supurgibekov, M. B.; Davies, H. M. L.; Sieler, J.; Zakharova, V. M. J. Org. Chem. 2013, 78, 4239.
[32] Loska, R.; Bukowsk, P. Org. Biomol. Chem. 2015, 13, 9872.
[33] Du, D.; Jiang, Y.; Xu, Q.; Tang, X.-Y.; Shi, M. ChemCatChem 2015, 7, 1366.
[34] Trost, B. M.; Debien, L. J. Am. Chem. Soc. 2015, 137, 11606.
[35] Zhang, Z.-M.; Xu, B.; Xu, S.; Wu, H.-H.; Zhang, J. Angew. Chem., Int. Ed. 2016, 55, 6324.
[36] Xu, B.; Zhang, Z.-M.; Xu, S.; Liu, B.; Xiao, Y.; Zhang, J. ACS Catal. 2017, 7, 210.
[37] Xu, B.; Zhang, Z.-M.; Liu, B.; Xu, S.; Zhou, L.-J.; Zhang, J. Chem. Commun. 2017, 53, 8152.
[38] Xu, S.; Zhang, Z.-M.; Xu, B.; Liu, B.; Liu, Y.; Zhang, J. J. Am. Chem. Soc. 2018, 140, 2272.
[39] Xu, S.; Liu, B.; Zhang, Z.-M.; Xu, B.; Zhang, J. Chin. J. Chem. 2018, 36, 421.
[40] Tang, L.-W.; Zhao, B.-J.; Dai, L.; Zhang, M.; Zhou, Z.-M. Chem.-Asian J. 2016, 11, 2470.
[41] Liu, B.; Zhang, Z.-M.; Xu, B.; Xu, S.; Wu, H.-H.; Liu Y.; Zhang, J. Org. Chem. Front. 2017, 4, 1772.
[42] Rabasa-Alcañiz, F.; Torres, J.; Sánchez-Roselló, M.; Tejero, T.; Merino, P.; Fustero, S.; del Pozo, C. Adv. Synth. Catal. 2017, 359, 3752.
[43] Bai, X.; Wu, C.; Ge, S.; Lu, Y. Angew. Chem., Int. Ed. 2020, 59, 2764.
[44] Sam, B.; Montgomery, T. P.; Krische, M. J. Org. Lett. 2013, 15, 3790.
[45] Holmes, M.; Nguyen, K. D.; Schwartz, L. A.; Luong, T.; Krische, M. J. J. Am. Chem. Soc. 2017, 139, 8114.

三氟甲基季碳中心的合成进展

Recent Advances of the Construction of Trifluoromethylated Quaternary Carbon Center

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Si Wen, Yuhao Ding, Qingyu Tian, Jin Ge, Guolin Cheng. Rhodium(III)-Catalyzed Synthesis of CF₃-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF₃-Imidoyl Sulfoxonium Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 291-300.
[2]	Xiaoying Jia, Jiaxia Pu, Lirong Han, Qinghan Li. Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 18-40.
[3]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[4]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[5]	Jiaxia Pu, Xiaoying Jia, Lirong Han, Qinghan Li. Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2591-2613.
[6]	Jing Liu, Jian Hao, Qilong Shen. Visible-Light-Promoted Direct Trifluoromethylation of Tryptophan-Containing Oligapeptides with YlideFluor [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1517-1524.
[7]	Rui Wang, Lang Gao, Cen Zhou, Xiao Zhang. Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1136-1145.
[8]	Yasir Mumtaz, Jie Liu, Xin Huang. Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 679-685.
[9]	Zujia Lu, Jian Qin, Jinting Wu, Wenli Cao, Baolong Kuang, Jianguo Zhang. Advances in the Synthesis of Energetic Compounds Based on 1,2,3-Triazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 526-554.
[10]	Shuyong Song, Senmiao Xu. Recent Progress in Selective C-F Bond Activation of Trifluoromethyl Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 411-425.
[11]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[12]	Jiajie Zhu, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang. Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3623-3634.
[13]	Zhaoming Hu, Jihong Wu, Jingjing Wu, Fanhong Wu. Research Progress on Direct Trifluoromethylselenylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 36-56.
[14]	Yun Shi, Ting Xiao, Dong Xia, Wenchao Yang. SCF₃ Radical Initiated Cascade Reaction of Unsaturated Hydrocarbon [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2715-2727.
[15]	Longyu Ran, Chengpan Zhang. An Overview of the Reactions with Trifluoromethyl Trifluoromethanesulfonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2045-2054.