Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles

Yang, Rui; Yu, Jin‐Tao; Sun, Song; Zheng, Qingheng; Cheng, Jiang

doi:10.1016/j.tetlet.2016.12.053

Cited by 25 publications

(24 citation statements)

References 83 publications

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“…Similarly, effective eﬀorts have been made to prepare 3‐aryl‐1 H ‐indole using 2‐vinylanilines as substrates (Scheme a). Including cyclization of 2‐vinylanilines used Cu(OAc) 2 as an accelerant, used PIFA as an oxidant . Recently, Li et al .…”

Section: Methodsmentioning

confidence: 99%

Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives

et al. 2020

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Herein, we report a non‐metal strategy for cyclization reactions of 2‐vinylanilines with/without isonitriles to synthesize 2‐aminoquinoline and 3‐aryl‐1H‐indole derivatives. A series of 2‐aminoquinolines were afforded in good to excellent yields in a direct, facile, and efficient approach by Se‐catalyzed isocyanide insertion with 2‐vinylanilines under an air atmosphere. This reaction not only used low toxicity Se as the catalyst, isocyanobenzene substrates were compatible too compared to previous report. Meanwhile, an intramolecular cyclization of 2‐vinylanilines was developed to give 3‐aryl‐1H‐indoles in moderate to good yields by using SeO2 as oxidant.

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Section: Methodsmentioning

confidence: 99%

Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives

et al. 2020

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“…Analytical data are consistent with reported values (305 mg, 76% yield). 37 1 H NMR (400 MHz, DMSO-d6) δ 11.37 (br s, 1H), 7.83 (d, J = 7.58 Hz, 1H), 7.65 – 7.76 (m, 3H), 7.45 (d, J = 8.07 Hz, 1H), 7.22 – 7.30 (m, 2H), 7.13 – 7.19 (m, 1H), 7.06 – 7.12 (m, 1H). 13 C NMR (101 MHz, DMSO-d6) d 162.0, 159.6, 137.3, 132.8, 132.7, 128.7, 128.6, 125.3, 123.9, 121.9, 120.1, 119.2, 116.1, 115.9, 115.1, 112.4.…”

Section: Synthesis Of Substratesmentioning

confidence: 99%

“…Analytical data are consistent with reported values (332 mg, 52% yield). 371 H NMR (400 MHz, DMSO-d6) δ 11.48 (br s, 1H), 7.79 (d, J =2.69 Hz, 1H), 7.67 (d, J = 7.09 Hz, 2H), 7.57 (dd, J = 2.45, 10.51 Hz, 1H), 7.40 – 7.49 (m, 3H), 7.20 – 7.28 (m, 1H), 7.01 (dt, J = 2.57, 9.11 Hz, 1H). 13 C NMR (101 MHz, DMSO-d6) d 159.1, 156.8, 135.8, 134.1, 129.3, 126.8, 125.9, 125.9, 125.6, 125.4, 116.4, 116.4, 113.5, 113.4, 110.2, 110.0, 104.3, 104.1.…”

Section: Synthesis Of Substratesmentioning

confidence: 99%

Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism

et al. 2018

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The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.

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“…Notably, the reaction was scaled up to gram-scale. The easy available 2-alkenylanilines underwent cyclization to 3-substituted indoles with Cu(OAc) 2 in stoichiometric amounts (Scheme 16) [38]. In fact the reaction worked better when copper itself acted as the oxidant, with respect to its use in catalytic amounts in the presence of an external oxidant.…”

Section: Cnmentioning

confidence: 99%

“…Cu(OAc)2 in stoichiometric amounts (Scheme 16) [38]. In fact the reaction worked better when copper itself acted as the oxidant, with respect to its use in catalytic amounts in the presence of an external oxidant.…”

Section: Cnmentioning

confidence: 99%

Recent Progress in the Transition Metal Catalyzed Synthesis of Indoles

Mancuso

Dalpozzo

2018

Catalysts

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Indole is the most frequently found heterocyclic core structures in pharmaceuticals, natural products, agrochemicals, dyes and fragrances. For about 150 years, chemists were absorbed in finding new and easier synthetic strategies to build this nucleus. Many books and reviews have been written, but the number of new syntheses that appear in the literature, make necessary continuous updates. This reviews aims to give a comprehensive overview on indole synthesis catalyzed by transition metals appeared in the literature in the years 2016 and 2017.

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Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles

Cited by 25 publications

References 83 publications

Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives

Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives

Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism

Recent Progress in the Transition Metal Catalyzed Synthesis of Indoles

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