Visible-Light-Promoted Metal-Free 3-Arylation of 2-Aryl-2H-­indazoles with Triarylsulfonium Salts

Anzai Shi; Panjie Xiang; Yanxuan Wu; Chang Ge; Yan Liu; Kai Sun; Bing Yu

doi:10.1055/a-1938-9550

Synlett, Table of Contents

Synlett 2023; 34(05): 457-464
DOI: 10.1055/a-1938-9550

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Special Edition Thieme Chemistry Journals Awardees 2022

Visible-Light-Promoted Metal-Free 3-Arylation of 2-Aryl-2H-indazoles with Triarylsulfonium Salts

Anzai Shi

^aGreen Catalysis Center, College of Chemistry, Zhengzhou University, Kexue Road No. 100, Zhengzhou 450001, P. R. of China

,

Panjie Xiang

^aGreen Catalysis Center, College of Chemistry, Zhengzhou University, Kexue Road No. 100, Zhengzhou 450001, P. R. of China

,

Yanxuan Wu

^aGreen Catalysis Center, College of Chemistry, Zhengzhou University, Kexue Road No. 100, Zhengzhou 450001, P. R. of China

,

Chang Ge

^aGreen Catalysis Center, College of Chemistry, Zhengzhou University, Kexue Road No. 100, Zhengzhou 450001, P. R. of China

,

Yan Liu

^cHenan International Joint Laboratory of Rare Earth Composite Material, College of Materials Engineering, Henan University of Engineering, Zhengzhou 451191, P. R. of China

,

Kai Sun∗

^aGreen Catalysis Center, College of Chemistry, Zhengzhou University, Kexue Road No. 100, Zhengzhou 450001, P. R. of China

^bCollege of Chemistry & Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China

,

Bing Yu∗

^aGreen Catalysis Center, College of Chemistry, Zhengzhou University, Kexue Road No. 100, Zhengzhou 450001, P. R. of China

› Author Affiliations

Abstract

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Abstract

An efficient approach for the photosynthesis of various arylated 2-aryl-2H-indazoles (38 examples) in moderate to good yields (up to 87% yield) under mild conditions was developed by employing 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as an inexpensive photocatalyst. This protocol features wide substrate scope, good functional group tolerance, and operational simplicity. In addition, the strategy was successfully applied to the late-stage modification of drug molecules, and the meaningful introduction of complex drugs to the skeleton of 2H-Indazole was achieved for the first time.

Key words

visible light - radical - metal-free - arylation - 2-aryl-2H-indazoles - triarylsulfonium salts

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References

References and Notes

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21 General Experimental Procedures for the Desired Product 3 The mixture of 2-aryl-2H-indazole (0.2 mmol), aryl sulfonium salt (0.3 mmol, 1.5 equiv.), DMAP (0.4 mmol, 2.0 equiv.), 4CzIPN (5 mol%), and MeCN (2.0 mL) were sequentially added in a 25 mL reaction vessel. Then the reaction vessel was exposed to 10 W blue LED irradiation at room temperature under N₂ atmosphere for 12 h. After reaction, the solvent was evaporated under vacuum, and all the crude products were purified by silica gel chromatography (petroleum ether/ethyl acetate = 30/1) as eluting solvent to give the desired products. Methyl 2-[2-Fluoro-4′-(2-phenyl-2H-indazol-3-yl)-(1,1′-biphenyl)-4-yl]propanoate (3r) White solid (56.7 mg, 63%); mp 142.5–143.2 °C. ¹H NMR (400 MHz, chloroform-d): δ = 7.83 (dd, J = 16.3, 8.6 Hz, 2 H), 7.65–7.57 (m, 2 H), 7.55–7.49 (m, 2 H), 7.49–7.33 (m, 7 H), 7.23–7.13 (m, 3 H), 3.80 (q, J = 7.2 Hz, 1 H), 3.73 (s, 3 H), 1.57 (d, J = 7.2 Hz, 3 H). ¹³C NMR (101 MHz, chloroform-d): δ = 174.4, 161.0, 149.1, 142.3 (d, J = 7.7 Hz), 140.2, 135.4, 135.0, 130.6 (d, J = 3.8 Hz), 129.7, 129.2 (d, J = 3.3 Hz), 129.1, 128.4, 127.1, 127.0, 126.8, 126.1, 123.7 (d, J = 3.4 Hz), 122.7, 121.8, 120.5, 117.8, 115.4 (d, J = 23.7 Hz), 52.3, 44.9, 18.4. ¹⁹F NMR (376 MHz, chloroform-d): δ = –117.19. HRMS (ESI-TOF): m/z [M + H]⁺ calcd for C₂₉H₂₄N₂O₂: 451.1816; found: 451.1821. 2-Phenyl-3-(4-{4-[2-(pyridin-2-yloxy)propoxy]phenoxy}phenyl)-2H-indazole (3s)White solid (72.9 mg, 71%); mp 171.1–172.3 °C. ¹H NMR (400 MHz, chloroform-d): δ = 8.21–8.16 (m, 1 H), 7.82 (d, J = 8.8 Hz, 1 H), 7.73 (d, J = 8.5 Hz, 1 H), 7.62–7.57 (m, 1 H), 7.53–7.22 (m, 8 H), 7.16 (ddd, J = 8.4, 6.6, 0.7 Hz, 1 H), 7.08–7.02 (m, 2 H), 7.01–6.93 (m, 4 H), 6.91–6.86 (m, 1 H), 6.77 (d, J = 8.3 Hz, 1 H), 5.65–5.58 (m, 1 H), 4.23 (dd, J = 9.9, 5.3 Hz, 1 H), 4.11 (dd, J = 9.8, 4.8 Hz, 1 H), 1.52 (d, J = 6.4 Hz, 3 H). ¹³C NMR (101 MHz, chloroform-d): δ = 163.1, 158.9, 155.7, 149.2, 149.0, 146.8, 140.3, 138.7, 135.1, 131.0, 129.0, 128.3, 127.0, 126.0, 123.7, 122.4, 121.6, 121.4, 120.5, 117.7, 117.3, 116.8, 115.9, 111.7, 71.0, 69.2, 17.0. HRMS (ESI-TOF): m/z [M + H]⁺ calcd for C₃₃H₂₈N₃O₃: 514.2125; found: 514.2136.
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Supplementary Material

Supporting Information

Visible-Light-Promoted Metal-Free 3-Arylation of 2-Aryl-2H-­indazoles with Triarylsulfonium Salts

Visible-Light-Promoted Metal-Free 3-Arylation of 2-Aryl-2H-indazoles with Triarylsulfonium Salts