Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins

Song, Xianheng; Luo, Xiang; Sheng, Jing; Li, Jianheng; Zhu, Zefeng; Du, Zhibo; Miao, Hui; Meng, Yu; Li, Mingkang; Zou, Yong

doi:10.1039/c9ra01909j

Cited by 20 publications

(13 citation statements)

References 64 publications

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“…Zou and co-workers [59] developed an effective copper-catalyzed intramolecular cross-dehydrogenative coupling of 2'-hydroxyl-3-arylcoumarins in aqueous medium, giving the CÀ O bond formation products with good yields [Eq. (44)].…”

Section: Coupling Of Cà H With Oà H Bond (Transition-metal Catalysis)mentioning

confidence: 99%

Recent Advances in Cross‐Dehydrogenative Couplings (CDC) of C−H Bond in Aqueous Media

Peng

Dong

2021

Adv Synth Catal

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To develop highly efficient synthetic reactions is quite important in organic chemistry. Cross dehydrogenative couplings (CDC) utilize C−H bonds of substrates to construct new C−X (X=C, S, O, N, P) bonds. For CDC, the pre‐functionalization of reaction substrates can be avoided and the C−X (X=C, S, O, N, P) bonds can be newly formed by simple and efficient synthesis routes. Meanwhile, water is increasingly used as a substitute for organic solvents in cross‐dehydrogenative coupling because of its rich content, non‐toxicity, and non‐ flammability. In recent years, organic chemists are devoted their efforts to explore the cross dehydrogenative couplings (CDC) in aqueous phase which feature high atom utilization rate and environmental friendliness. Herein, we summarized the recent advances in the construction of C−C, C−S, C−O, C−N, and C−P bonds through CDC reactions of C−H bonds in water.

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Section: Coupling Of Cà H With Oà H Bond (Transition-metal Catalysis)mentioning

confidence: 99%

Recent Advances in Cross‐Dehydrogenative Couplings (CDC) of C−H Bond in Aqueous Media

Peng

Dong

2021

Adv Synth Catal

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“…Song et al disclosed a copper-mediated system for the synthesis of natural coumestans 206 from 2'-hydroxyl-3-arylcoumarin 205 through intramolecular cross-dehydrogenative CÀ O coupling. [60] The catalyst used in this strategy was Cu(OAc) 2 (20 mol%) along with 1, 10-phen (20 mol%) as the ligand and the reaction was carried out in DMSO/H 2 O (3.1) at 135°C for 18 h in air atmosphere (Scheme 66). Differently substituted 2'hydroxyl-3-arylcoumarin with electron-donating groups, a naphthyl group and Cl were well tolerated under the reaction conditions and afforded moderate to good yield.…”

Section: Synthesis Of Coumestansmentioning

confidence: 99%

“…(Reproduced from Ref. [60] Copyright (2019), with permission from Royal Society of Chemistry.) Scheme 68.…”

Section: Cà P Bond Formationmentioning

confidence: 99%

“…Song et al . disclosed a copper‐mediated system for the synthesis of natural coumestans 206 from 2’‐hydroxyl‐3‐arylcoumarin 205 through intramolecular cross‐dehydrogenative C−O coupling [60] . The catalyst used in this strategy was Cu(OAc) 2 (20 mol%) along with 1, 10‐phen (20 mol%) as the ligand and the reaction was carried out in DMSO/H 2 O (3.1) at 135 °C for 18 h in air atmosphere (Scheme 66).…”

Section: C−o Bond Formationmentioning

confidence: 99%

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Copper‐Catalyzed Cross‐Dehydrogenative Coupling Reactions

et al. 2021

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Copper-catalyzed organic reactions have received wide attention due to the high relative abundance of copper, its cheap price, low toxicity, eco-friendliness, sustainable nature, and versatility as a catalyst. Copper catalysts are widely used in cross-dehydrogenative coupling and have found wide applications in heterocyclic chemistry. This review focuses on the recent advances in the synthesis of biologically important compounds such as nitrogen heterocycles, amines, amides, imines, and alkynes using copper-catalyzed cross-dehydrogenative coupling and covers literature from 2018 to 2020.

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“…Zou and co-workers demonstrated the synthesis of coumestans 217 from 2 0 -hydroxyl-3-arylcoumarins 216. 95 Under optimized conditions (Cu(OAc) 2 (20 mol%), 1,10-phen (20 mol%), DMSO/H 2 O (3 : 1) at 135 C, 18 h) (Scheme 84). The reaction was carried out under air and a wide functional group tolerance was observed.…”

Section: C-o Bond Formationmentioning

confidence: 99%

Progress and prospects in copper-catalyzed C–H functionalization

et al. 2020

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Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins

Abstract: A copper-catalyzed intramolecular cross dehydrogenative C–O coupling reaction of 2′-hydroxyl-3-arylcoumarins was developed.

Cited by 20 publications

References 64 publications

Recent Advances in Cross‐Dehydrogenative Couplings (CDC) of C−H Bond in Aqueous Media

Recent Advances in Cross‐Dehydrogenative Couplings (CDC) of C−H Bond in Aqueous Media

Copper‐Catalyzed Cross‐Dehydrogenative Coupling Reactions

Progress and prospects in copper-catalyzed C–H functionalization

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