https://doi.org/10.1039/d2cc05000e ·
Journal: Chemical Communications, 2022, №93, p.12900-12912
Publisher: Royal Society of Chemistry (RSC)
Authors: Yan Liu, Lin Zuo, Tianyi Shang, Zhenling Wang, Bing Yu
Abstract
Polyfluoroaryl compounds belong to privileged moieties and engender distinct properties in many pharmaceuticals, agrochemicals, and materials. In this review, state-of-the-art in photocatalytic polyfluoroarylation has been present since 2014.
Funders
- Natural Science Foundation of Henan Province
- National Natural Science Foundation of China
List of references
- Ni, Chem. Soc. Rev., № 45, с. 5441
https://doi.org/10.1039/C6CS00351F
- Liang, Angew. Chem., Int. Ed., № 52, с. 8214
https://doi.org/10.1002/anie.201206566
- Cheng, Angew. Chem., Int. Ed., № 59, с. 5880
https://doi.org/10.1002/anie.201907662
- Xing, Chin. J. Chem., № 40, с. 323
https://doi.org/10.1002/cjoc.202100709
- Wang, Org. Chem. Front., № 8, с. 2079
https://doi.org/10.1039/D0QO01629B
- Purser, Chem. Soc. Rev., № 37, с. 320
https://doi.org/10.1039/B610213C
- Wang, Chem. Rev., № 114, с. 2432
https://doi.org/10.1021/cr4002879
- Inoue, ACS Omega, № 5, с. 10633
https://doi.org/10.1021/acsomega.0c00830
- Ogawa, iScience, № 23, с. 101467
https://doi.org/10.1016/j.isci.2020.101467
- Zhao, Tetrahedron Lett., № 59, с. 180
https://doi.org/10.1016/j.tetlet.2017.12.022
- Koike, Org. Biomol. Chem., № 17, с. 5413
https://doi.org/10.1039/C9OB00734B
- Liu, Chin. J. Org. Chem., № 40, с. 2322
https://doi.org/10.6023/cjoc202003055
- Lee, Angew. Chem., Int. Ed., № 58, с. 11171
https://doi.org/10.1002/anie.201902243
- Sap, Chem. Soc. Rev., № 50, с. 8214
https://doi.org/10.1039/D1CS00360G
- Feng, Org. Chem. Front., № 9, с. 3598
https://doi.org/10.1039/D2QO00551D
- Shi, Org. Chem. Front., № 9, с. 4192
https://doi.org/10.1039/D2QO00762B
- An, Chin. J. Org. Chem., № 41, с. 4554
https://doi.org/10.6023/cjoc202110037
- Qin, Chin. J. Org. Chem., № 40, с. 3177
https://doi.org/10.6023/cjoc202005016
- Cheng, Chin. Chem. Lett.
https://doi.org/10.1016/j.cclet.2022.06.048
- Cheng, Chin. Chem. Lett., № 32, с. 1437
https://doi.org/10.1016/j.cclet.2020.09.044
- Studer, Angew. Chem., Int. Ed., № 51, с. 8950
https://doi.org/10.1002/anie.201202624
- Alonso, Chem. Rev., № 115, с. 1847
https://doi.org/10.1021/cr500368h
- Xiao, Chem. Soc. Rev., № 50, с. 6308
https://doi.org/10.1039/D1CS00200G
- Wang, Chin. J. Chem., № 40, с. 59
https://doi.org/10.1002/cjoc.202100599
- Wang, Chin. J. Org. Chem., № 40, с. 1901
https://doi.org/10.6023/cjoc202001012
- Ma, Chem. Rev., № 108, с. PR1
https://doi.org/10.1021/cr800221v
- Ma, Chem. Rev., № 104, с. 6119
https://doi.org/10.1021/cr030143e
- Ma, Front. Chem., № 10, с. 953978
https://doi.org/10.3389/fchem.2022.953978
- Zhang, J. Catal., № 413, с. 214
https://doi.org/10.1016/j.jcat.2022.06.033
- Liu, Synthesis, с. 1919
- Wang, ACS Sustainable Chem. Eng., № 7, с. 10154
https://doi.org/10.1021/acssuschemeng.9b02178
- Tang, Tetrahedron Lett., № 58, с. 2127
https://doi.org/10.1016/j.tetlet.2017.04.055
- Xu, Chem. Rev., № 115, с. 731
https://doi.org/10.1021/cr500193b
- Li, Acta Chim. Sin., № 76, с. 913
https://doi.org/10.6023/A18070306
- Zhang, Acta Chim. Sin., № 75, с. 744
https://doi.org/10.6023/A17050202
- Zhang, Chin. J. Chem., № 38, с. 169
https://doi.org/10.1002/cjoc.201900364
- Hardy, Asian J. Org. Chem., № 8, с. 591
https://doi.org/10.1002/ajoc.201900004
- Zhang, Sci. China: Chem., № 62, с. 525
https://doi.org/10.1007/s11426-018-9402-x
- Wang, Chin. J. Org. Chem., № 40, с. 1805
https://doi.org/10.6023/cjoc202003048
- McAtee, Trends Chem., № 1, с. 111
https://doi.org/10.1016/j.trechm.2019.01.008
- Narayanam, Chem. Soc. Rev., № 40, с. 102
https://doi.org/10.1039/B913880N
- Romero, Chem. Rev., № 116, с. 10075
https://doi.org/10.1021/acs.chemrev.6b00057
- Xuan, Angew. Chem., Int. Ed., № 51, с. 6828
https://doi.org/10.1002/anie.201200223
- Crisenza, Nat. Commun., № 11, с. 803
https://doi.org/10.1038/s41467-019-13887-8
- Michelin, Curr. Opin. Green Sustainable Chem., № 10, с. 40
https://doi.org/10.1016/j.cogsc.2018.02.009
- Ravelli, Chem. Soc. Rev., № 38, с. 1999
https://doi.org/10.1039/b714786b
- Yoon, Nat. Chem., № 2, с. 527
https://doi.org/10.1038/nchem.687
- Chatterjee, Acc. Chem. Res., № 49, с. 2284
https://doi.org/10.1021/acs.accounts.6b00248
- Barata-Vallejo, ACS Catal., № 8, с. 7287
https://doi.org/10.1021/acscatal.8b02066
- Koike, Chem, № 4, с. 409
https://doi.org/10.1016/j.chempr.2017.11.004
- Li, Angew. Chem., Int. Ed., № 55, с. 4436
https://doi.org/10.1002/anie.201509073
- Charpentier, Chem. Rev., № 115, с. 650
https://doi.org/10.1021/cr500223h
- Chen, Org. Chem. Front., № 9, с. 1152
https://doi.org/10.1039/D1QO01504D
- Ni, Chem. Rev., № 115, с. 765
https://doi.org/10.1021/cr5002386
- Chu, Acc. Chem. Res., № 47, с. 1513
https://doi.org/10.1021/ar4003202
- Xie, Chin. J. Chem., № 38, с. 202
https://doi.org/10.1002/cjoc.201900424
- Caraiman, J. Phys. Chem. A, № 108, с. 978
https://doi.org/10.1021/jp0307194
- Senaweera, J. Am. Chem. Soc., № 136, с. 3002
https://doi.org/10.1021/ja500031m
- Lu, J. Am. Chem. Soc., № 138, с. 15805
https://doi.org/10.1021/jacs.6b08620
- Liu, Inorg. Chem. Front., № 3, с. 861
https://doi.org/10.1039/C5QI00269A
- Toriumi, Chem. – Eur. J., № 27, с. 12635
https://doi.org/10.1002/chem.202101813
- Tian, J. Am. Chem. Soc., № 140, с. 17612
https://doi.org/10.1021/jacs.8b09790
- Xu, Angew. Chem., Int. Ed., № 59, с. 4009
https://doi.org/10.1002/anie.201911819
- Xia, Org. Lett., № 22, с. 1742
https://doi.org/10.1021/acs.orglett.0c00020
- Xie, Angew. Chem., Int. Ed., № 56, с. 7266
https://doi.org/10.1002/anie.201700135
- Nicholls, Chem. Commun., № 54, с. 4589
https://doi.org/10.1039/C8CC02244E
- Wang, J. Org. Chem., № 84, с. 6895
https://doi.org/10.1021/acs.joc.9b00708
- Sun, Angew. Chem., Int. Ed., № 60, с. 10557
https://doi.org/10.1002/anie.202015596
- Juliá, Chem. Rev., № 122, с. 2292
https://doi.org/10.1021/acs.chemrev.1c00558
- Niu, Org. Lett., № 24, с. 916
https://doi.org/10.1021/acs.orglett.1c04267
- Singh, Chem. Sci., № 6, с. 7206
https://doi.org/10.1039/C5SC03013G
- Priya, J. Am. Chem. Soc., № 140, с. 16020
https://doi.org/10.1021/jacs.8b09156
- Singh, Chem. Sci., № 7, с. 6796
https://doi.org/10.1039/C6SC02422J
- Meyer, ACS Catal., № 6, с. 369
https://doi.org/10.1021/acscatal.5b02410
- Senaweera, J. Am. Chem. Soc., № 138, с. 2520
https://doi.org/10.1021/jacs.5b13450
- Day, J. Org. Chem., № 86, с. 7928
https://doi.org/10.1021/acs.joc.1c00169
- Dewanji, Chem. – Eur. J., № 21, с. 12295
https://doi.org/10.1002/chem.201502298
- Weidlich, Adv. Synth. Catal., № 362, с. 376
https://doi.org/10.1002/adsc.201901126
- Bo, Chin. J. Catal., № 43, с. 2388
https://doi.org/10.1016/S1872-2067(22)64140-8
- Chan, Chem. Rev., № 122, с. 1485
https://doi.org/10.1021/acs.chemrev.1c00383
- Qin, Organometallics, № 40, с. 2246
https://doi.org/10.1021/acs.organomet.0c00813
Publications that cite this publication
Radical reactions enabled by polyfluoroaryl fragments: photocatalysis and beyond
Mikhail O. Zubkov, Alexander D. Dilman
https://doi.org/10.1039/d3cs00889d ·
2024, Chemical Society Reviews, №9, p.4741-4785
Scopus
WoS
Crossref citations:0
Radical cascade cyclization of 1,<i>n</i>-enynes under photo/electrochemical conditions
Zhenzhi Cai, Sven Trienes, Kairui Liu, Lutz Ackermann, Yan Zhang
https://doi.org/10.1039/d3qo01482g
2023, Organic Chemistry Frontiers, №22, p.5735-5745
Scopus
WoS
Crossref citations:4
Quantifying flattening distortion on the thermodynamics and kinetics of electron transfers of Cu(<scp>i</scp>) photoredox catalysts
Christian Sandoval-Pauker, Gabriela Molina-Aguirre, Dino Villagrán, Balazs Pinter
https://doi.org/10.1039/d4qi00613e
2024, Inorganic Chemistry Frontiers
Scopus
WoS
Crossref citations:0
Photoredox/copper-catalyzed <i>gem</i>-difluoroalkylation-cyanation of 1,3-enynes
Yachen Wang, Shuai Liu, Yangen Huang
https://doi.org/10.1039/d4ob00602j ·
2024, Organic & Biomolecular Chemistry
Scopus
WoS
Crossref citations:0
Find all citations of the publication
About this publication
Number of citations | 8 |
Number of works in the list of references | 81 |
Journal indexed in Scopus | Yes |
Journal indexed in Web of Science | Yes |