Visible-Light Promoted Preparation of Trifluoromethylated Tetrahydrofuran and Tetrahydropyran

doi:10.6023/cjoc201808048

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 200-206.DOI: 10.6023/cjoc201808048 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Articles

可见光促进合成三氟甲基取代的四氢呋喃和四氢吡喃

王娜^a,b, 顾强帅^c, 程永峰^a, 李磊^a, 李忠良^c, 郭臻^b, 刘心元^a

a 南方科技大学化学系和格拉布斯研究院深圳 518055;
b 太原理工大学材料科学与工程学院新材料界面科学与工程教育部重点实验室太原 030024;
c 南方科技大学前沿与交叉科学研究院深圳 518055

收稿日期:2018-08-31 修回日期:2018-09-26 发布日期:2018-10-20
通讯作者: 顾强帅, 郭臻, 刘心元 E-mail:guqs@sustc.edu.cn;guozhen@tyut.edu.cn;liuxy3@sustc.edu.cn
基金资助:
国家自然科学基金（Nos.21722203，21831002，21801116和21572096）、深圳市科技研发资金（Nos.JCYJ20170412152435366和JCYJ-20170307105638498）、广东省自然科学基金（No.2018A030310083）和深圳市诺贝尔奖科学家实验室（No.C17213101）资助项目.

Visible-Light Promoted Preparation of Trifluoromethylated Tetrahydrofuran and Tetrahydropyran

Wang Na^a,b, Gu Qiang-Shuai^c, Cheng Yong-Feng^a, Li Lei^a, Li Zhong-Liang^c, Guo Zhen^b, Liu Xin-Yuan^a

a Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055;
b Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education, College of Materials Science & Engineering, Taiyuan University of Technology, Shanxi 030024;
c SUSTech Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518055

Received:2018-08-31 Revised:2018-09-26 Published:2018-10-20
Contact: 10.6023/cjoc201808048 E-mail:guqs@sustc.edu.cn;guozhen@tyut.edu.cn;liuxy3@sustc.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21722203, 21831002, 21801116, and 21572096), the Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy, and New Material Industries (Nos. JCYJ20170412152435366, JCYJ20170307105638498), the Natural Science Foundation of Guangdong Province (No. 2018A030310083) and the Shenzhen Nobel Prize Scientists Laboratory Project (No. C17213101).

1. Visible-Light Promoted Preparation of Trifluoromethylated Tetrahydrofuran and Tetrahydropyran.PDF(984KB)

Abstract

An efficient protocol for facile access to trifluoromethylated tetrahydrofuran and tetrahydropyran has been developed under visible light irradiation conditions via radical 1,2-alkoxyl-trifluoromethylation of unactivated alkene. It features the use of readily commercially available and operatively simple trifluoromethanesulfonyl chloride as a trifluoro- methyl radical source, thus making the protocol potentially appealing for practical preparation.

Key words: trifluoromethanesulfonyl chloride, tetrahydrofuran, tetrahydropyran, visible light, alkoxyl-trifluoromethylation

Cite this article

Wang Na, Gu Qiang-Shuai, Cheng Yong-Feng, Li Lei, Li Zhong-Liang, Guo Zhen, Liu Xin-Yuan. Visible-Light Promoted Preparation of Trifluoromethylated Tetrahydrofuran and Tetrahydropyran[J]. Chin. J. Org. Chem., 2019, 39(1): 200-206.

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[1] (a) Guéret, S. M.; Brimble, M. A. Nat. Prod. Rep. 2010, 27, 1350.
(b) Lorente, A.; Lamariano-Merketegi, J.; Albericio, F.; Álvarez, M. Chem. Rev. 2013, 113, 4567.
(c) Xu, Y.; Wang, W.; Yang, J.; Li, X.; Meng, Q. Chin. J. Org. Chem. 2016, 36, 724(in Chinese). (徐阳荣, 王文智, 杨静静, 李新利, 孟庆国, 有机化学, 2016, 36, 724.)
[2] (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
(b) Nasir, N. M.; Ermanis, K.; Clarke, P. A. Org. Biomol. Chem. 2014, 12, 3323.
(c) Tikad, A.; Delbrouck, J. A.; Vincent, S. P. Chem.-Eur. J. 2016, 22, 9456.
[3] (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(b) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
(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) Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.
[4] (a) Jeschke, P. ChemBioChem 2004, 5, 570.
(b) Jeschke, P. Pest Manage. Sci. 2010, 66, 10.
(c) Fujiwara, T.; O'Hagan, D. J. Fluorine Chem. 2014, 167, 16.
[5] Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Blackwell Publishing Ltd, West Sussex, 2009.
[6] (a) McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555.
(b) Dolbier, W. R. Chem. Rev. 1996, 96, 1557.
(c) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
(d) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
(e) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.
(f) Prakash, G. K. S.; Wang, F. In Organic Chemistry-Breakthroughs and Perspectives, Eds.:Ding, K.; Dai, L.-X., Wiley-VCH, Weinheim, 2012.
(g) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
(h) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513.
(i) Alonso, C.; Martínez de Marigorta, E.; Rubiales, G.; Palacios, F. Chem. Rev. 2015, 115, 1847.
(j) Charpentier, J.; Früh, N.; Togni, A. Chem. Rev. 2015, 115, 650.
(k) Huang, L.; Zheng, S.-C.; Tan, B.; Liu, X.-Y. Chem.-Eur. J. 2015, 21, 6718.
(l) Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731.
(m) Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826.
(n) Groult, H.; Leroux, F. R.; Tressaud, A. Modern Synthesis Processes and Reactivity of Fluorinated Compounds, Elsevier Inc., 2017.
(o) Hui, R.; Zhang, S.; Tan, Z.; Wu, X.; Feng, B. Chin. J. Org. Chem. 2017, 37, 3060(in Chinese). (惠人杰, 张士伟, 谭政, 吴小培, 冯柏年, 有机化学, 2011, 37, 3060.)
(p) Song, H.-X.; Han, Q.-Y.; Zhao, C.-L.; Zhang, C.-P. Green Chem. 2018, 20, 1662.
[7] (a) Magueur, G.; Crousse, B.; Charneau, S.; Grellier, P.; Bégué, J.-P.; Bonnet-Delpon, D. J. Med. Chem. 2004, 47, 2694.
(b) Frezza, M.; Balestrino, D.; Soulère, L.; Reverchon, S.; Queneau, Y.; Forestier, C.; Doutheau, A. Eur. J. Org. Chem. 2006, 2006, 4731.
(c) Chen, J.-L.; You, Z.-W.; Qing, F.-L. J. Fluorine Chem. 2013, 155, 143.
(d) Kim, S.; Kim, E.; Lee, W.; Hong, J. H. Nucleosides Nucleotides Nucleic Acids 2014, 33, 747.
(e) Kollatos, N.; Manta, S.; Dimopoulou, A.; Parmenopoulou, V.; Triantakonstanti, V. V.; Kellici, T.; Mavromoustakos, T.; Schols, D.; Komiotis, D. Carbohydr. Res. 2015, 407, 170.
(f) Shibata, H.; Tsuchikawa, H.; Hayashi, T.; Matsumori, N.; Murata, M.; Usui, T. Chem.-Asian J. 2015, 10, 915.
(g) Achmatowicz, M. M.; Allen, J. G.; Bio, M. M.; Bartberger, M. D.; Borths, C. J.; Colyer, J. T.; Crockett, R. D.; Hwang, T.-L.; Koek, J. N.; Osgood, S. A.; Roberts, S. W.; Swietlow, A.; Thiel, O. R.; Caille, S. J. Org. Chem. 2016, 81, 4736.
[8] (a) Yang, B.; Xu, X.-H.; Qing, F.-L. Chin. J. Chem. 2016, 34, 465.
(b) Li, T.; Yu, P.; Lin, J.-S.; Zhi, Y.; Liu, X.-Y. Chin. J. Chem. 2016, 34, 490.
[9] (a) Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462.
(b) Beniazza, R.; Molton, F.; Duboc, C.; Tron, A.; McClenaghan, N. D.; Lastécouères, D.; Vincent, J.-M. Chem. Commun. 2015, 51, 9571.
(c) Wang, Y.; Jiang, M.; Liu, J.-T. Adv. Synth. Catal. 2016, 358, 1322.
(d) Cheng, Y.-F.; Dong, X.-Y.; Gu, Q.-S.; Yu, Z.-L.; Liu, X.-Y. Angew. Chem., Int. Ed. 2017, 56, 8883.
[10] Noto, N.; Koike, T.; Akita, M. J. Org. Chem. 2016, 81, 7064.
[11] (a) Foulard, G.; Brigaud, T.; Portella, C. J. Fluorine Chem. 1998, 91, 179.
(b) Lin, R.; Sun, H.; Yang, C.; Shen, W.; Xia, W. Chem. Commun. 2015, 51, 399.
(c) Ryzhakov, D.; Jarret, M.; Guillot, R.; Kouklovsky, C.; Vincent, G. Org. Lett. 2017, 19, 6336.
[12] (a) Heaton, C. A.; Powell, R. L. J. Fluorine Chem. 1989, 45, 86.
(b) Kamigata, N.; Fukushima, T.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1989, 1559.
(c) Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.
(d) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
(e) Chachignon, H.; Guyon, H.; Cahard, D. Beilstein J. Org. Chem. 2017, 13, 2800.
[13] (a) Yu, P.; Lin, J.-S.; Li, L.; Zheng, S.-C.; Xiong, Y.-P.; Zhao, L.-J.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2014, 53, 11890.
(b) Yu, P.; Zheng, S.-C.; Yang, N.-Y.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2015, 54, 4041.
(c) Lin, J.-S.; Dong, X.-Y.; Li, T.-T.; Jiang, N.-C.; Tan, B.; Liu, X.-Y. J. Am. Chem. Soc. 2016, 138, 9357.
(d) Li, L.; Li, Z.-L.; Wang, F.-L.; Guo, Z.; Cheng, Y.-F.; Wang, N.; Dong, X.-W.; Fang, C.; Liu, J.; Hou, C.; Tan, B.; Liu, X.-Y. Nat. Commun. 2016, 7, 13852.
(e) Li, L.; Li, Z.-L.; Gu, Q.-S.; Wang, N.; Liu, X.-Y. Sci. Adv. 2017, 3, e1701487.
(f) Lin, J.-S.; Wang, F.-L.; Dong, X.-Y.; He, W.-W.; Yuan, Y.; Chen, S.; Liu, X.-Y. Nat. Commun. 2017, 8, 14841.
(g) Li, X.-T.; Gu, Q.-S.; Dong, X.-Y.; Meng, X.; Liu, X.-Y. Angew. Chem., Int. Ed. 2018, 57, 7668.
[14] (a) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527.
(b) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
(c) Teplý, F. Collect. Czech. Chem. Commun. 2011, 76, 859.
(d) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.
(e) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
(f) Hopkinson, M. N.; Sahoo, B.; Li, J.-L.; Glorius, F. Chem.-Eur. J. 2014, 20, 3874.
(g) Koike, T.; Akita, M. Inorg. Chem. Front. 2014, 1, 562.
(h) Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355.
(i) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.
(j) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
(k) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898.
(l) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
(m) Staveness, D.; Bosque, I.; Stephenson, C. R. J. Acc. Chem. Res. 2016, 49, 2295.
(n) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.; MacMillan, D. W. C. Nat. Rev. Chem. 2017, 1, 52.
(o) Cao, M.-Y.; Ren, X.; Lu, Z. Tetrahedron Lett. 2015, 56, 3732.
[15] (a) Huang, L.; Ye, L.; Li, X.-H.; Li, Z.-L.; Lin, J.-S.; Liu, X.-Y. Org. Lett. 2016, 18, 5284.
(b) Li, Z.-L.; Li, X.-H.; Wang, N.; Yang, N.-Y.; Liu, X.-Y. Angew. Chem., Int. Ed. 2016, 55, 15100.
(c) Wang, N.; Li, L.; Li, Z.-L.; Yang, N.-Y.; Guo, Z.; Zhang, H.-X.; Liu, X.-Y. Org. Lett. 2016, 18, 6026.
(d) Wang, N.; Wang, J.; Guo, Y.-L.; Li, L.; Sun, Y.; Li, Z.; Zhang, H.-X.; Guo, Z.; Li, Z.-L.; Liu, X.-Y. Chem. Commun. 2018, 54, 8885.
[16] Kim, E.; Choi, S.; Kim, H.; Cho, E. J. Chem.-Eur. J. 2013, 19, 6209.
[17] (a) Jiang, H.; Huang, C.; Guo, J.; Zeng, C.; Zhang, Y.; Yu, S. Chem.-Eur. J. 2012, 18, 15158.
(b) Jiang, H.; Cheng, Y.; Zhang, Y.; Yu, S. Eur. J. Org. Chem. 2013, 2013, 5485.

可见光促进合成三氟甲基取代的四氢呋喃和四氢吡喃

Visible-Light Promoted Preparation of Trifluoromethylated Tetrahydrofuran and Tetrahydropyran

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