Recent Advances in the Decarboxylative Fluoroalkylation of Fluoroalkyl Carboxylic Acids

doi:10.6023/cjoc202208017

Abstract

Decarboxylation of fluoroalkyl carboxylic acid derivatives is an effective way to obtain fluoroalkyl radicals, which subsequently participates in the tandem and addition reactions of olefins, isonitriles and aromatic (hetero) rings, providing an important method to obtain divegent fluorine-containing molecules. A variety of fluoroalkyl cyclic compounds such as phenanthridines, dihydroflavonoid, quinolinones and indolones could be constructed using the tandem reaction initiated by fluoroalkyl radicals generated from fluoroalkyl carboxylic acids. The research progress of radical reactions induced by decarboxylation of fluoroalkyl carboxylic acids in recent years is summarized, which includes reaction design, reaction mechanism and outlook.

Key words: fluoroalkylation, decarboxylative reaction, carboxylic acid

Cite this article

Yuxi Zhu, Ting Xiao, Dong Xia, Wenchao Yang. Recent Advances in the Decarboxylative Fluoroalkylation of Fluoroalkyl Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4067-4077.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 20

Scheme 1. Radical cascade reaction of unsaturated hydrocarbon initiated by decarboxylation of fluoroalkyl carboxylic acids

Scheme 2. Synthesis of 6-gem-difluoromethylenated phenanthridine

Scheme 3. Synthesis of difluorooxindoles and thiodifluorooxindole derivatives

Scheme 4. Synthesis of difluoroquinolinone derivatives

Scheme 5. Synthesis of chroman-4-ones and indanones

Scheme 6. Synthesis of quinazolinone derivatives

Scheme 7. Silver-catalyzed C—H trifluoromethylation of arenes

Scheme 8. Difluoromethylation of heteroarenes

Scheme 9. Silver-catalyzed monofluoroalkylation of heteroarenes

Scheme 10. gem-Aryldifluoromethylation of quinoxalin-2(1H)- ones

Scheme 11. Ag-catalyzed gem-aryldifluoromethylation of N- heteroarenes

Scheme 12. gem-Aryldifluoromethylation of quinoline N-oxides

Scheme 13. gem-Aryldifluoromethylation and arylthiodifluoromethylation of coumarins

Scheme 14. Pd-catalyzed decarboxylative meta-C—H difluoromethylation

Scheme 15. Catalytic decarboxylative fluorination of α,α-difluoroarylacetic acids

Scheme 16. Decarboxylative alkynylation of α,α-difluoroarylacetic acids

Scheme 17. Decarboxylative alkylation and thiolation of α,α-difluoroarylacetic acids

Scheme 18. Decarboxylative alkylation of α,α-difluoro- arylacetic acids

Scheme 19. Hydroaryldifluoromethylation of alkenes with α,α-difluoroarylacetic acids

Scheme 20. Hydroaryldifluoromethylation of alkenes with α-fluoro carboxylic acids

References 30

[31]	(a) Yang, B.; Xu, X.-H.; Qing, F.-L. Org. Lett. 2016, 18, 5956. pmid: 27805816
	(b) Guo, C.; Han, X.; Feng, Y.; Liu, Z.; Li, Y.; Liu, H.; Zhang, L.; Dong, Y.; Li, X. J. Org. Chem. 2022, 87, 9232. doi: 10.1021/acs.joc.2c00965 pmid: 27805816
[1]	(a) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513. doi: 10.1021/ar4003202
	(b) Ni, C.; Hu, J. Chem. Soc. Rev. 2016, 45, 5441. doi: 10.1039/C6CS00351F
	(c) Zhang, X.; Tang, P. Sci. China: Chem. 2019, 62, 525.
	(d) Feng, Z.; Xiao, Y.-L.; Zhang, X. Acc. Chem. Res. 2018, 51, 2264. doi: 10.1021/acs.accounts.8b00230
	(e) Zhang, C.-P.; Chen, Q.-Y.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C. Chem. Soc. Rev. 2012, 41, 4536. doi: 10.1039/c2cs15352a
[2]	(a) Dong, D.-Q.; Yang, H.; Shi, J.-L.; Si, W.-J.; Wang, Z.-L.; Xu, X.-M. Org. Chem. Front. 2020, 7, 2538. doi: 10.1039/D0QO00567C
	(b) Shao, X.; Xu, C.; Lu, L.; Shen, Q. Acc. Chem. Res. 2015, 48, 1227. doi: 10.1021/acs.accounts.5b00047
	(c) Wang, Z.; Sun, Y.; Shen, L.-Y.; Yang, W.; Meng, F.; Li, P. Org. Chem. Front. 2022, 9, 853. doi: 10.1039/D1QO01512E
	(d) Wang, J.; Liu, H. Chin. J. Org. Chem. 2011, 31, 1785. (in Chinese)
	( 王江, 柳红, 有机化学, 2011, 31, 1785.)
	(e) Zhang, J.; Jin, C.; Zhang, Y. Chin. J. Org. Chem. 2014, 34, 662. (in Chinese)
	( 张霁, 金传飞, 张英俊, 有机化学, 2014, 34, 662.) doi: 10.6023/cjoc201310039
[3]	(a) Aguilar Troyano, F. J.; Merkens, K.; Anwar, K.; Gomez-Suarez, A. Angew. Chem., Int. Ed. 2021, 60, 1098. doi: 10.1002/anie.202010157 pmid: 34306801
	(b) Shi, Y.; Xiao, H.; Xu, X.-H.; Huang, Y. Org. Biomol. Chem. 2018, 16, 8472. doi: 10.1039/C8OB02457J pmid: 34306801
	(c) Xiang, J.; Shang, M.; Kawamata, Y.; Lundberg, H.; Reisberg, S. H.; Chen, M.; Mykhailiuk, P.; Beutner, G.; Collins, M. R.; Davies, A.; Del Bel, M.; Gallego, G. M.; Spangler, J. E.; Starr, J.; Yang, S.; Blackmond, D. G.; Baran, P. S. Nature 2019, 573, 398. doi: 10.1038/s41586-019-1539-y pmid: 34306801
	(d) Brigham, C. E.; Malapit, C. A.; Lalloo, N.; Sanford, M. S. ACS Catal. 2020, 10, 8315. doi: 10.1021/acscatal.0c02950 pmid: 34306801
	(e) Mei, W.; Kong, Y.; Yan, G. Org. Chem. Front. 2021, 8, 5516. doi: 10.1039/D1QO00775K pmid: 34306801
[4]	(a) Yang, W.-C.; Feng, J.-G.; Wu, L.; Zhang, Y.-Q. Adv. Synth. Catal. 2019, 361, 1700. doi: 10.1002/adsc.201801355
	(b) Si, Y.-F.; Lv, Q.-Y.; Yu, B. Adv. Synth. Catal. 2021, 363, 4640. doi: 10.1002/adsc.202100807
	(c) Lv, Y.; Cui, H.; Meng, N.; Yue, H.; Wei, W. Chin. Chem. Lett. 2022, 33, 97. doi: 10.1016/j.cclet.2021.06.068
	(d) Yang, W.-C.; Zhang, M.-M.; Feng, J.-G. Adv. Synth. Catal. 2020, 362, 4446. doi: 10.1002/adsc.202000636
	(e) Shang, T.; Lu, L.; Cao, Z.; Liu, Y.; He, W.; Yu, B. Chem. Commun. 2019, 55, 5408. doi: 10.1039/C9CC01047E
[5]	Wan, W.; Ma, G.; Li, J.; Chen, Y.; Hu, Q.; Li, M.; Jiang, H.; Deng, H.; Hao, J. Chem. Commun. 2016, 52, 1598. doi: 10.1039/C5CC09179A
[6]	(a) Wan, W.; Li, J.; Ma, G.; Chen, Y.; Jiang, H.; Deng, H.; Hao, J. Org. Biomol. Chem. 2017, 15, 5308. doi: 10.1039/C7OB00955K
	(b) Li, Y.-L.; Wang, J.-B.; Wang, X.-L.; Cao, Y.; Deng, J. Eur. J. Org. Chem. 2017, 2017, 6052. doi: 10.1002/ejoc.201701248
[7]	Huang, C.-M.; Li, J.; Wang, S.-H.; Ai, J.-J.; Liu, X.-Y.; Rao, W.-D.; Wang, S.-Y. J. Org. Chem. 2021, 86, 8437. doi: 10.1021/acs.joc.1c00965
[8]	Zhao, F.; Guo, S.; Zhang, Y.; Sun, T.; Yang, B.; Ye, Y.; Sun, K. Org. Chem. Front. 2021, 8, 6895. doi: 10.1039/D1QO01425K
[9]	Zhou, Y.; Xiong, Z.; Qiu, J.; Kong, L.; Zhu, G. Org. Chem. Front. 2019, 6, 1022. doi: 10.1039/C9QO00136K
[10]	Cui, Q.; Teng, F.; Yang, H.; Xun, C.; Huang, W.; Lu, Z.; Zhu, M.; Ouyang, W.; He, W.-M. Chem.-Asian J. 2022, 17, e202101139.
[11]	Barata-Vallejo, S.; Postigo, A. Chem.-Eur. J. 2020, 26, 11065. doi: 10.1002/chem.202000856
[12]	Shi, G.; Shao, C.; Pan, S.; Yu, J.; Zhang, Y. Org. Lett. 2015, 17, 38. doi: 10.1021/ol503189j
[13]	Proctor, R. S. J.; Phipps, R. J. Angew. Chem., Int. Ed. 2019, 58, 13666. doi: 10.1002/anie.201900977
[14]	Truong, T. T.; Christensen, S. B.; Nielsen, J. Chem.-Eur. J. 2017, 23, 18125. doi: 10.1002/chem.201704261 pmid: 28945302
[15]	Guo, C.; Liu, Z.; Li, X.; Han, X.; Li, Y.; Liu, H.; Zhang, L.; Li, X.; Dong, Y. Chem. Commun. 2022, 58, 1147. doi: 10.1039/D1CC06466E
[16]	Guo, C.; Han, X.; Li, X.; Diao, Z.; Li, X.; Dong, Y. Asian J. Org. Chem. 2022, 11, e202100663.
[17]	Galal, S. A.; Khairat, S. H. M.; Ragab, F. A. F.; Abdelsamie, A. S.; Ali, M. M.; Soliman, S. M.; Mortier, J.; Wolber, G.; El Diwani, H. I. Eur. J. Med. Chem. 2014, 86, 122. doi: 10.1016/j.ejmech.2014.08.048
[18]	Sun, K.; Xiao, F.; Yu, B.; He, W.-M. Chin. J. Catal. 2021, 42, 1921. doi: 10.1016/S1872-2067(21)63850-0
[19]	Hong, G.; Yuan, J.; Fu, J.; Pan, G.; Wang, Z.; Yang, L.; Xiao, Y.; Mao, P.; Zhang, X. Org. Chem. Front. 2019, 6, 1173. doi: 10.1039/C9QO00105K
[20]	Gao, Y.; Zhao, L.; Xiang, T.; Li, P.; Wang, L. RSC Adv. 2020, 10, 10559. doi: 10.1039/D0RA02059A
[21]	Xie, X.; Zhang, Y.; Hao, J.; Wan, W. Org. Biomol. Chem. 2020, 18, 400. doi: 10.1039/C9OB02586C
[22]	Gao, Y.; Li, L.; Liu, J.; Wang, L.; Wang, M. Synthesis 2021, 53, 1636. doi: 10.1055/a-1343-5642
[23]	(a) Yu, D.; Suzuki, M.; Xie, L.; Morris-Natschke, S. L.; Lee, K.-H. Med. Res. Rev. 2003, 23, 322. doi: 10.1002/med.10034
	(b) Bras, G. L.; Radanyi, C.; Peyrat, J.-F.; Brion, J.-D.; Alami, M.; Marsaud, V.; Stella, B.; Renoir, J.-M. J. Med. Chem. 2007, 50, 6189. doi: 10.1021/jm0707774
	(c) Hassan, M. Z.; Osman, H.; Ali, M. A.; Ahsan, M. J. Eur. J. Med. Chem. 2016, 123, 236. doi: 10.1016/j.ejmech.2016.07.056
	(d) Anamika, D.; Utreja, D.; Ekta; Jain, N.; Sharma, S. Curr. Org. Chem. 2019, 22, 2509. doi: 10.2174/1385272822666181029102140
	(e) Yang, W.; Yang, S.; Li, P.; Wang, L. Chem. Commun. 2015, 51, 7520. doi: 10.1039/C5CC00878F
[24]	(a) Chen, Z.; Bai, X.; Sun, J.; Xu, Y. J. Org. Chem. 2020, 85, 7674. doi: 10.1021/acs.joc.0c00113
	(b) Chen, Z.; Sun, J.; Ke, Z.; Huang, X.; Li, Z. Org. Chem. Front. 2022, 9, 757. doi: 10.1039/D1QO01609A
[25]	Zhao, H.-X.; Ma, G.-B.; Xie, X.-Y.; Wang, Y.; Hao, J.; Wan, W. Chem. Commun. 2019, 55, 3927. doi: 10.1039/C9CC00984A
[26]	(a) Mizuta, S.; Stenhagen, I. S. R.; O’Duill, M.; Wolstenhulme, J.; Kirjavainen, A. K.; Forsback, S. J.; Tredwell, M.; Sandford, G.; Moore, P. R.; Huiban, M.; Luthra, S. K.; Passchier, J.; Solin, O.; Gouverneur, V. Org. Lett. 2013, 15, 2648. doi: 10.1021/ol4009377 pmid: 27440264
	(b) Zhou, M.; Ni, C.; He, Z.; Hu, J. Org. Lett. 2016, 18, 3754. doi: 10.1021/acs.orglett.6b01779 pmid: 27440264
	(c) Zhang, Q.-W.; Brusoe, A. T.; Mascitti, V.; Hesp, K. D.; Blakemore, D. C.; Kohrt, J. T.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 9758. doi: 10.1002/anie.201604793 pmid: 27440264
[27]	(a) Chen, F.; Hashmi, A. S. K. Org. Lett. 2016, 18, 2880. doi: 10.1021/acs.orglett.6b01188 pmid: 27267868
	(b) Li, X.; Li, S.; Sun, S.; Yang, F.; Zhu, W.; Zhu, Y.; Wu, Y.; Wu, Y. Adv. Synth. Catal. 2016, 358, 1699. doi: 10.1002/adsc.201501028 pmid: 27267868
[28]	(a) Wang, Y.; Zhao, H.; Xie, X.; Jiang, H.; Deng, H.; Hao, J.; Wan, W. Synth. Commun. 2019, 49, 2961.
	(b) Zhang, Y.; Wang, Q.; Peng, Y.; Gong, H.; Chen, H.; Deng, H.; Hao, J.; Wan, W. Org. Biomol. Chem. 2021, 19, 7024. doi: 10.1039/D1OB01165K
[29]	Debien, L.; Quiclet-Sire, B.; Zard, S. Z. Acc. Chem. Res. 2015, 48, 1237. doi: 10.1021/acs.accounts.5b00019
[30]	Li, X.; Zhang, R. H.; Zhang, X. F.; Zhu, P. Y.; Yao, T. L. Chem.-Asian J. 2020, 15, 1175. doi: 10.1002/asia.202000059

氟烷基羧酸的脱羧氟烷基化反应研究进展