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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 1: 85 - 110

DOI: https://doi.org/10.6023/cjoc202307004

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Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds

  • Yukun Jin ,
  • Baoyi Ren ,
  • Fushun Liang
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  • a College of Science, Shenyang University of Chemical Technology, Shenyang 110142
    b College of Chemistry, Liaoning University, Shenyang 110036
*E-mail: ;
E-mail:

Received date: 2023-07-08

  Revised date: 2023-08-12

  Online published: 2023-09-08

Supported by

Natural Science Foundation of Liaoning Province(2021-MS-254)

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Abstract

The unique properties of difluorinated compounds have attracted widespread attention in the fields of medicine and material sciences. The conversion of inexpensive and easily available trifluoromethyl groups into difluoro groups is of great importance in organic synthesis. However, there still exist great challenges in the selective cleavage of C—F bonds, because the dissociation energy of single C—F bond in trifluoromethyl group is much higher than that of the C—F bond in the difluoro unit of the generated product. Thus, the selective cleavage of C—F bond is difficult to control, which can easily lead to excessive defluorination. Compared with the traditional thermal reaction, the visible-light irradiated reaction provides an alternative pathway to achieve C—F cleavage more efficiently and selectively. The research progress on the selective cleavage of C—F bonds mediated by visible light in the past three years is summarized and its future perspective is prospected.

Key words： photocatalysis; free radical; C—F fracture; germinal difluoro-compound; synthesis

Cite this article

Yukun Jin , Baoyi Ren , Fushun Liang . Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds[J]. Chinese Journal of Organic Chemistry, 2024 , 44(1) : 85 -110 . DOI: 10.6023/cjoc202307004

References

[1]
(a) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Acen?a, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
[1]
(b) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
[1]
(c) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
[1]
(d) Yamauchi, Y.; Fukuhara, T.; Hara, S.; Senboku, H. Synlett 2008, 438.
[2]
(a) Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496.
[2]
(b) Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496.
[3]
Ye, J. H.; Bellotti, P.; Heusel, C.; Glorius, F. Angew. Chem. Int. Ed. 2022, 61, e202115456.
[4]
(a) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
[4]
(b) Wang, N.; Mei, H.; Dhawan, G.; Zhang, W.; Han, J.; Soloshonok, V. A. Molecules 2023, 28, 3651.
[4]
(c) He, J.; Li, Z.; Dhawan, G.; Zhang, W.; Sorochinsky, A. E.; Butler, G.; Soloshonok, V. A.; Han, J. Chin. Chem. Lett. 2023, 34, 107578.
[5]
Bremer, M.; Kirsch, P.; Klasen-Memmer, M.; Tarumi, K. Angew. Chem. Int. Ed. 2013, 52, 8880.
[6]
Tian, P.; Feng, C.; Loh, T.-P. Nat. Commun. 2015, 6, 7472.
[7]
Feng, X.-T.; Ren, J.-X.; Gao, X.; Min, Q.-Q.; Zhang, X. Angew. Chem. Int. Ed. 2022, 61, e202210103.
[8]
(a) G?litz, P.; de Meijere, A. Angew. Chem. Int. Ed. 1977, 16, 854.
[8]
(b) Prakash, G. S.; Hu, J.; Wang, Y.; Olah, G. A. J. Fluorine Chem. 2005, 126, 527.
[9]
Chen, K.; Berg, N.; Gschwind, R.; Ko?nig, B. J. Am. Chem. Soc. 2017, 139, 18444.
[10]
(a) Song, S.; Senmiao, Xu, S. Chin. J. Org. Chem. 2023, 43, 411 (in Chinese).
[10]
(宋树勇, 徐森苗, 有机化学, 2023, 43, 411.)
[10]
(b) Vogt, D. B.; Seath, C. P.; Wang, H.; Jui, N. T. J. Am. Chem. Soc. 2019, 141, 13203.
[11]
O'Hagan, D. ChemInform 2008, 39.
[12]
Luo, C.; Bandar, J. S. J. Am. Chem. Soc. 2019, 141, 14120.
[13]
Zhang, X.; Ning, Y.; Liu, Z.; Li, S.; Zanoni, G.; Bi, X. ACS Catal. 2022, 12, 8802.
[14]
(a) R?ckl, J. L.; Robertson, E. L.; Lundberg, H. Org. Biomol. Chem. 2022, 20, 6707.
[14]
(b) Yamauchi, Y.; Fukuhara, T.; Hara, S.; Senboku, H. Synlett 2008, 438.
[15]
(a) Uneyama, K.; Amii, H. J. Fluorine Chem. 2002, 114, 127.
[15]
(b) Fuchibe, K.; Ohshima, Y.; Mitomi, K.; Akiyama, T. Org. Lett. 2007, 9, 1497.
[16]
(a) Scott, V. J.; ?elenligil-?etin, R.; Ozerov, O. V. J. Am. Chem. Soc. 2005, 127, 2852.
[16]
(b) Forster, F.; Metsa?nen, T. T.; Irran, E.; Hrobárik, P.; Oestreich, M. J. Am. Chem. Soc. 2017, 139, 16334.
[17]
Liang, F.-S. J. Liaoning Univ., Nat. Sci. Ed. 2017, 44, 138 (in Chinese).
[17]
(梁福顺, 辽宁大学学报: 自然科学版, 2017, 44, 138.)
[18]
Li, S.; Shu, W. Chem. Commun. 2022, 58, 1066.
[19]
Zhou, L. Molecules 2021, 26, 7051.
[20]
Zhao, F.; Zhou, W.; Zuo, Z. Adv. Synth. Catal. 2022, 364, 234.
[21]
Xu, W.; Zhang, Q.; Shao, Q.; Xia, C.; Wu, M. Asian J. Org. Chem. 2021, 10, 2454.
[22]
Ai, H.-J.; Ma, X.; Song, Q.; Wu, X.-F. Sci. Chin. Chem. 2021, 64, 1630.
[23]
Yan, G.; Qiu, K.; Guo, M. Org. Chem. Front. 2021, 8, 3915.
[24]
An, X.; Zhang, F.; Huang, L.; Yang, Y.; Liu, Z. Chin. J. Org. Chem. 2021, 41, 4554 (in Chinese).
[24]
(安欣妮, 张峰, 黄林, 杨毅, 有机化学, 2021, 41, 4554.)
[25]
Li, Z.; Qiu, X.; Lou, J.; Wang, Q. Chin. J. Org. Chem. 2021, 41, 4192 (in Chinese).
[25]
(李志清, 邱晓阳, 楼江, 王强, 有机化学, 2021, 41, 4192.)
[26]
Simur, T. T.; Ye, T.; Yu, Y.-J.; Zhang, F.-L.; Wang, Y-F. Chin. Chem. Lett. 2022, 33, 1193.
[27]
Jing, Q.; Sun, J. Chemistry 2022, 85, 203 (in Chinese).
[27]
(荆祺, 孙京, 化学通报, 2022, 85, 203.)
[28]
(a) Neha, H.; Naaz, A.; Prassanawar, S.; Guchhait, K.; Panda, D. ACS Omega 2018, 3, 1955.
[28]
(b) Park, B. K.; Kitteringham, N. R.; O'Neill, P. M. Annu. Rev. Pharmacol. 2001, 41, 443.
[29]
Sap, J. B.; Straathof, N. J.; Knauber, T.; Meyer, C. F.; Me?debielle, M.; Buglioni, L.; Genicot, C.; Trabanco, A. S. A.; Noe?l, T.; Am Ende, C. W. J. Am. Chem. Soc. 2020, 142, 9181.
[30]
Yan, S.-S.; Liu, S.-H.; Chen, L.; Bo, Z.-Y.; Jing, K.; Gao, T.-Y.; Yu, B.; Lan, Y.; Luo, S.-P.; Yu, D.-G., Chem 2021, 7, 3099.
[31]
Wang, J.; Wang, Y.; Liang, Y.; Zhou, L.; Liu, L.; Zhang, Z. Angew. Chem. Int. Ed. Engl. 2022, e202215062.
[32]
Liu, C.; Li, K.; Shang, R. ACS. Catal. 2022, 12, 4103.
[33]
Hendy, C. M.; Pratt, C. J.; Jui, N. T.; Blakey, S. B. Org. Lett. 2023, 25, 1397.
[34]
Xu, J.; Liu, J.-W.; Wang, R.; Yang, J.; Zhao, K.-K.; Xu, H.-J. ACS. Catal. 2023, 13, 7339.
[35]
Yuan, X.; Zhuang, K.-Q.; Cui, Y.-S.; Qin, L.-Z.; Sun, Q.; Duan, X.; Chen, L.; Zhu, N.; Li, G.; Qiu, J.-K.; Guo, K. Commun. Chem. 2020, 3, 98.
[36]
Luo, Y.-C.; Tong, F. F.; Zhang, Y.; He, C.-Y.; Zhang, X. J. Am. Chem. Soc. 2021, 143, 13971.
[37]
Kynman, A. E.; Elghanayan, L. K.; Desnoyer, A. N.; Yang, Y.; Severy, L.; Di Giuseppe, A.; Tilley, T. D.; Maron, L.; Arnold, P. L. Chem. Sci. 2022, 13, 14090.
[38]
Maekawa, Y.; Nambo, M.; Yokogawa, D.; Crudden, C. M. J. Am. Chem. Soc. 2020, 142, 15667.
[39]
(a) Zhang, X.; Cao, S. Tetrahedron Lett. 2017, 58, 375.
[39]
(b) Pan, Y.; Qiu, J.; Silverman, R. B. J. Med. Chem. 2003, 46, 5292.
[39]
(c) Lang, S. B.; Wiles, R. J.; Kelly, C. B.; Molander, G. A. Angew. Chem. Int. Ed. 2017, 56, 15073.
[39]
(d) Jaroschik, F. Chem. Eur. J. 2018, 24, 14572.
[39]
(e) Fujiwara, T.; O'Hagan, D. J. Fluorine Chem. 2014, 167, 16.
[40]
Zhang, Z.; Yu, W.; Wu, C.; Wang, C.; Zhang, Y.; Wang, J. Angew. Chem. Int. Ed. 2016, 55, 273.
[41]
(a) Bégué, J.-P.; Bonnet-Delpon, D. Bouvet, D.; Rock, M. H. J. Org. Chem. 1996, 61, 9111.
[41]
(b) Fuchibe, K.; Takahashi, M.; Ichikawa, J. Angew. Chem. Int. Ed. 2012, 51, 12059.
[41]
(c) Yang, J.; Mao, A.; Yue, Z.; Zhu, W.; Luo, X.; Zhu, C.; Xiao, Y.; Zhang, J. Chem. Commun. 2015, 51, 8326.
[41]
(d) Fujita, T.; Takazawa, M.; Sugiyama, K.; Suzuki, N.; Ichikawa, J. Org. Lett. 2017, 19, 588.
[42]
(a) Chen, H.; Anand, D.; Zhou, L. Asian. J. Org. Chem. 2019, 8, 661.
[42]
(b) Lang, S. B.; Wiles, R. J.; Kelly, C. B.; Molander, G. A. Angew. Chem. Int. Ed. 2017, 56, 15073.
[42]
(c) Chen, G.; Wang, L.; Liu, X.; Liu, P. Adv. Synth. Catal. 2020, 362, 2990.
[43]
Xiang, P.; He, L.; Li, H.; Qi, Z.; Zhang, M.; Fu, Q.; Wei, J.; Du, X.; Yi, D.; Wei, S. Tetrahedron Lett. 2020, 61, 152369.
[44]
Gladkov, A. A.; Chernov, G. N.; Levin, V. V.; Kokorekin, V. A.; Dilman, A. D. Org. Lett. 2021, 23, 9645.
[45]
Hu, Q.-P.; Cheng, J.; Wang, Y.; Shi, J.; Wang, B.-Q.; Hu, P.; Zhao, K.-Q.; Pan, F. Org. Lett. 2021, 23, 4457.
[46]
Hu, X.; Ding, A.; Xu, D.; Guo, H. Chem. Commun (Camb.) 2021, 57, 7441.
[47]
Gao, Q.-S.; Niu, Z.; Chen, Y.; Sun, J.; Han, W.-Y.; Wang, J.-Y.; Yu, M.; Zhou, M.-D. Org. Lett. 2021, 23, 6153.
[48]
Shi, J.; Guo, L.-Y.; Hu, Q.-P.; Liu, Y.-T.; Li, Q.; Pan, F. Org. Lett. 2021, 23, 8822.
[49]
Yan, S.; Yu, W.; Zhang, J.; Fan, H.; Lu, Z.; Zhang, Z.; Wang, T. J. Org. Chem. 2022, 87, 1574.
[50]
Luo, C.; Zhou, Y.; Chen, H.; Wang, T.; Zhang, Z. B.; Han, P.; Jing, L. H. Org. Lett. 2022, 24, 4286.
[51]
Yang, C.; Chen, J.; Li., X.; Meng., L.; Wang, K.; Sun, W.; Fan, B. Acta Chim. Sinica 2023, 81, 1 (in Chinese).
[51]
(杨春晖, 陈景超, 李新汉, 孟丽, 王凯民, 孙蔚青, 樊保敏, 化学学报, 2023, 81, 1.)
[52]
Xu, W; Xia, C.; Shao, Q.; Zhang, Q.; Liu, M.; Zhang, H.; Wu, M. Org. Chem. Front. 2022, 9, 4949.
[53]
Atriardi, S. R.; Kim, J. Y.; Anita, Y.; Woo, S. K. B. Korean Chem. Soc. 2023, 44, 50.
[54]
Yang, C.; Chen, J.; Li, X.; Yang, X.; Zhu, Y.; Wu, S.; Zeng, G.; Wang, K.; Fan, B. ChemistrySelect 2022, 7, e202201188.
[55]
Du, D.; Peng, H.; He, L.; Bai, S.; Li, Z.; Teng, H. Org. Biomol. Chem. 2022, 20, 9313.
[56]
Sun, Z.; Zhou, L. J. Org. Chem. 2022, 87, 4801.
[57]
Zeng, W.; Li, W.; Chen, H.; Zhou, L. Org. Lett. 2022, 24, 3265.
[58]
Zeng, W.; Li, L.; Wang, C.; Wang, D.; Zhou, L. Adv. Synth. Catal. 2022, 364, 3310.
[59]
Wang, Q.; Yue, L.; Bao, Y.; Wang, Y.; Kang, D.; Gao, Y.; Yuan, Z. J. Org. Chem. 2022, 87, 8237.
[60]
Yuan, W.-Q.; Liu, Y.-T.; Ni, Y.-Q.; Liu, Y.-Z.; Pan, F. Org. Chem. Front. 2022, 9, 4867.
[61]
Li, W.; Chen, X.; Zhou, L. Org. Lett. 2022, 24, 5946.
[62]
Gao, P.; Cui, L.; Zhang, G.; Chen, F. Catal. Sci. Technol. 2023, 13, 1628.
[63]
Zhang, G.; Wang, L.; Cui, L.; Gao, P.; Chen, F. Org. Biomol. Chem. 2023, 21, 294.
[64]
Guo, Y.-Q.; Wang, R.; Song, H.; Liu, Y.; Wang, Q. Org. lett. 2020, 22, 709.
[65]
Supranovich, V. I.; Levin, V. V.; Kokorekin, V. A.; Dilman, A. D. Adv. Synth. Catal. 2021, 363, 2888.
[66]
Xia, G.-D.; He, Y.-Y.; Zhang, J.; Liu, Z.-K.; Gao, Y.; Hu, X.-Q. Chem. Commun. 2022, 58, 6733.
[67]
Anand, D.; Sun, Z.; Zhou, L. Org. Lett. 2020, 22, 2371.
[68]
Chen, Y.; Ni, N.; Cheng, D.; Xu, X. Tetrahedron. Lett. 2020, 61, 152425.
[69]
Qi, J.; Zhang, F. L.; Jin, J. K.; Zhao, Q.; Li, B.; Liu, L. X.; Wang, Y. F. Angew. Chem. Int. Ed. 2020, 59, 12876.
[70]
Li, F.; Pei, C.; Koenigs, R. M. Angew. Chem. Int. Ed. 2022, 61, e202111892.
[71]
Yue, F.; Dong, J.; Liu, Y.; Wang, Q. Org. Lett. 2021, 23, 7306.
[72]
Guo, Y.; Cao, Y.; Song, H.; Liu, Y.; Wang, Q. Chem. Commun (Camb.) 2021, 57, 9768.
[73]
Yue, F.; Liu, J.; Ma, H.; Liu, Y.; Dong, J.; Wang, Q. Org. Lett. 2022, 24, 4019.
[74]
Yue, W.-J.; Day, C. S.; Martin, R. J. Am. Chem. Soc. 2021, 143, 6395.
[75]
Tu, J.-L.; Yang, J.-W.; Xu, W.; Su, M.; Liu, F. Org. Chem. Front. 2021, 8, 6405.
[76]
Li, C. Y.; Ma, Y.; Lei, Z. W.; Hu, X. G. Org. Lett. 2021, 23, 8899.
[77]
Zhang, Y.; Zhang, Y.; Shen, X. Chem. Catal. 2021, 1, 423.
[78]
Tian, J.; Sun, Z.; Li, W.; Wang, D.; New. J. Chem. 2022, 46, 8545.
[79]
Zhang, Y.; Niu, Y.; Guo, Y.; Wang, J.; Zhang, Y.; Liu, S.; Shen, X. Angew. Chem. Int. Ed. 2022, 61, e202212201.
[80]
Wang, J. X.; Ge, W.; Fu, M. C.; Fu, Y. Org. Lett. 2022, 24, 1471.
[81]
Wang, B.; Wang, C.-T.; Li, X.-S.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2022, 24, 6566.
[82]
Zhao, Y.; Empel, C.; Liang, W.; Koenigs, R. M.; Patureau, F. W. Org. Lett. 2022, 24, 8753.
[83]
Chen, B.; Yu, K.; Wu, X.-F. Org. Biomol. Chem. 2022, 20, 5264.
[84]
Qin, T.; Xu, C.; Zhang, G.; Zhang, Q. Org. Chem. Front. 2023, 10, 1981.
[85]
Xu, Y.; Wang, S.; Liu, Z.; Guo, M.; Lei, A. Chem. Commun. 2023, 59, 3707.
[86]
Jin, J.; MacMillan, D. W. Nature 2015, 525, 87.
[87]
Campbell, M. W.; Polites, V. C.; Patel, S.; Lipson, J. E.; Majhi, J.; Molander, G. A. J. Am. Chem. Soc. 2021, 143, 19648.
[88]
Ye, J. H.; Bellotti, P.; Heusel, C.; Glorius, F. Angew. Chem. Int. Ed. Engl. 2022, 61, e202115456.
[89]
Liu, C.; Shen, N.; Shang, R. Nat. Commun. 2022, 13, 354.
[90]
Shreiber, S. T.; Granados, A.; Matsuo, B.; Majhi, J.; Campbell, M. W.; Patel, S.; Molander, G. A. Org. Lett. 2022, 24, 8542.
[91]
Matsuo, B.; Majhi, J.; Granados, A.; Sharique, M.; Martin, R. T.; Gutierrez, O.; Molander, G. A. Chem. Sci. 2023, 14, 2379.
[92]
Ghosh, S.; Qu, Z. W.; Pradhan, S.; Ghosh, A.; Grimme, S.; Chatterjee, I. Angew. Chem. Int. Ed. Engl. 2022, 61, e202115272.
[93]
Ghosh, S.; Qu, Z. W.; Roy, S.; Grimme, S.; Chatterjee, I. Chemistry 2023, 29, e202203428.
[94]
Xu, P.; Wang, X. Y.; Wang, Z.; Zhao, J.; Cao, X. D.; Xiong, X. C.; Yuan, Y. C.; Zhu, S.; Guo, D.; Zhu, X. Org. Lett. 2022, 24, 4075.
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