Metal‐Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones

Yao, Qiuli; Liu, Wenbo; Liu, Peng; Ren, Lizhu; Fang, Xuehong; Li, Chao‐Jun

doi:10.1002/ejoc.201801650

Cited by 13 publications

(9 citation statements)

References 52 publications

(14 reference statements)

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“…This compound is known, and the data reported here are consistent with the literature. 33 1 H NMR (400 MHz, CDCl 3 ) δ 7.72 (s, 1H), 7.68 (d, J = 7.8 Hz, 1H), 7.20 (d, J = 7.7 Hz, 1H), 2.56 (s, 3H), 2.30 (s, 6H). 13 1 H NMR (400 MHz, CDCl 3 ) δ 7.82 (s, 1H), 7.63 (d, J = 7.9 Hz, 1H), 7.21 (d, J = 7.9 Hz, 1H), 2.47 (s, 3H), 2.32 (s, 3H).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…This compound is known, and the data reported here are consistent with the literature. 33 1 H NMR (400 MHz, CDCl 3 ) δ 7.98 (d, J = 2.1 Hz, 1H), 7.86 (dd, J = 8.6, 2.1 Hz, 1H), 6.96 (d, J = 8.6 Hz, 1H), 3.96 (s, 3H), 2.55 (s, 3H). 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 195.7, 158.7, 130.9, 130.6, 128.7, 122.8, 111.2, 56.3, 26.3.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…This compound is known, and the data reported here are consistent with the literature. 33 1 H NMR (400 MHz, CDCl 3 ) δ 7.80 (d, J = 8.5 Hz, 1H), 7.75 (s, 1H), 6.82 (d, J = 8.5 Hz, 1H), 3.87 (s, 3H), 2.53 (s, 3H), 2.23 (s, 3H). 13 1-(4-Chloro-3-nitrophenyl)ethenone (33).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…33 1 H NMR (400 MHz, CDCl 3 ) δ 7.80 (d, J = 8.5 Hz, 1H), 7.75 (s, 1H), 6.82 (d, J = 8.5 Hz, 1H), 3.87 (s, 3H), 2.53 (s, 3H), 2.23 (s, 3H). 13 1-(4-Chloro-3-nitrophenyl)ethenone (33). 54 mg, 54% General Procedure A (49 mg, 49% General Procedure B), white solid.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 3 more Smart Citations

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

Yang

Yan

et al. 2021

J. Org. Chem.

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A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 2 more Smart Citations

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

Yang

Yan

et al. 2021

J. Org. Chem.

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“…Similar results were found when α-ketoacids were used as the acyl source (Scheme , eqs c and d). Li’s group reported the photoinduced acylation reaction using 1,2-diketones as acyl source via a radical procedure . To investigate the interference of light on our strategy, the reaction under dark conditions was carried out.…”

mentioning

confidence: 99%

Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones

et al. 2021

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The indole scaffold is a ubiquitous and useful substructure, and extensive investigations have been conducted to construct the indole framework and/or realize indole modification. Nevertheless, the direct selective functionalization on the benzenoid core must overcome the high activity of the C-3 position and still remains highly challenging. Herein, a palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group was developed. This strategy usually is considered as a practical strategy for the preparation of acylated indoles because indoline can be easily converted to indole under oxidation conditions. In particular, our strategy greatly improved the alkacylation yield of indolines for which only an unsatisfactory yield could be achieved in the previous studies. Furthermore, the reaction can be scaled up to gram level in the standard reaction conditions with a much lower palladium loading (1 mol %).

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The Photoinduced Metal‐Free Hydrotrifluoromethylation of Vinyl Phosphonates or Phosphine Oxides

et al. 2019

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We describe a simple and metal‐free photochemical strategy for the direct hydrotrifluoromethylation of vinyl phosphonates or phosphine oxides by sodium triflinate under ultraviolet or visible light irradiation. Acetone and diacetyl were used as radical initiators to generate CF3 radicals that were efficiently added to vinyl phosphonates or phosphine oxide to yield β‐trifluoromethylated phosphorus compounds without the use of any catalyst. A broad scope of substrates scope is demonstrated in moderate to excellent yields. Mechanistic experiments were performed to study the source of hydrogen; the results indicate that H2O in the solvent or additive is the primary hydrogen source.

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Metal‐Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones

Cited by 13 publications

References 52 publications

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones

The Photoinduced Metal‐Free Hydrotrifluoromethylation of Vinyl Phosphonates or Phosphine Oxides

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