2020
DOI: 10.1002/cctc.202000284
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Copper‐Catalyzed Aerobic Oxidative Amination of Indole Derivatives via Single‐Electron Transfer

Abstract: An efficient and clean approach for the oxidative amination of indole derivatives with phenothiazines is developed under copper‐catalyzed aerobic conditions. The reaction is carried out via the cross‐coupling of indole radical cation and phenothiazine radical in air. This approach offers a new perspective in the application of phenothiazine as a nitrogen group source for C−N bond formation reactions.

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Cited by 24 publications
(14 citation statements)
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“…It is worth mentioning that the structure of product 4ba was further determined by singlecrystal structure X-ray diffraction. 19 2-Aminobenzenethiol with a halogen at the C4 position also provided the target product in an 84% yield (4ga). In addition, 2-amino-4-chlorobenzenethiol could react with different kinds of substituted 2-(1Hindol-3-yl)cyclohexanones to produce the corresponding products in moderate yields (4ha−4la).…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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“…It is worth mentioning that the structure of product 4ba was further determined by singlecrystal structure X-ray diffraction. 19 2-Aminobenzenethiol with a halogen at the C4 position also provided the target product in an 84% yield (4ga). In addition, 2-amino-4-chlorobenzenethiol could react with different kinds of substituted 2-(1Hindol-3-yl)cyclohexanones to produce the corresponding products in moderate yields (4ha−4la).…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…1-(5-Fluoro-1-methyl-1H-indol-3-yl)-10H-phenothiazine (3aj). Eluent: petroleum ether/EtOAc = 20:1, R f = 0.40, pale-yellow solid (29.1 mg, 42% yield), mp 161−163 °C; 1 H NMR (400 MHz, DMSO-d 6 ) δ 7.62 (s, 1H), 7.59−7.56 (m, 1H), 7.33 (s, 1H), 7.10 (t, J = 9.0 Hz, 1H), 7.05−6.94 (m, 5H), 6.89 (t, J = 7.4 Hz, 1H), 6.81 (t, J = 7.4 Hz, 1H), 6.70 (d, J = 8.0 Hz, 1H), 3.89 (s, 3H); 13 C{ 1 H} NMR (100 MHz, DMSO-d 6 ) δ 157.4 (d,J = 232.6 Hz),142.1,139.4,133.7,131.0,129.6,127.3,126.6 (d,J = 9.7 Hz),126.1,125.0,122.3,122.0,120.5,118.2,117.6,115.8,111.5 (d,J = 9.5 Hz),110.0,109.7,103.6 (d,J = 23.5 Hz), 33.0; 19 1-(5-Chloro-1-methyl-1H-indol-3-yl)-10H-phenothiazine (3ak). Eluent: petroleum ether/EtOAc = 20:1, R f = 0.39, pale-yellow solid (43.4 mg, 60% yield), mp 145−147 °C; 1 H NMR (400 MHz, DMSO-d 6 ) δ 7.61 (s, 1H), 7.59 (d,J = 8.4 Hz,1H),7.33 (s,1H),2H),4H),6.89 (t,J = 7.6 Hz,1H),6.81 (t,J = 7.4 Hz,1H),6.69 (d,J = 8.0 Hz,1H), 3.89 (s, 3H); 13 C{ 1 H} NMR (100 MHz, DMSO-d 6 ) δ 142.…”
Section: ■ Conclusionmentioning
confidence: 99%
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“…From an economic point of view, copper catalysis would provide a more appealing alternative . In particular, air is typically compatible with copper catalysis, establishing an environmentally friendly synthetic method in line with green chemistry. Our oxidative coupling strategy provides a powerful tool for the bond-forming reactions avoiding prefunctionalization of C–H bonds. , Taking advantage of the above two concepts, we envisioned that a concise copper/air system could be capable of steering oxidative C–H/C–H [4 + 2] annulation of 3-arylindoles containing an alkynyl group to yield polycyclic heteroaromatic hydrocarbons (Scheme c).…”
mentioning
confidence: 99%