Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

Wu, Yufeng; Zhou, Guangli; Meng, Qingwei; Tang, Xiaofei; Liu, Guangzhi; Yin, Hang; Zhao, Jianzhang; Yang, Fan; Yu, Zongyi; Luo, Yi

doi:10.1021/acs.joc.8b01710

Cited by 36 publications

(15 citation statements)

References 121 publications

(171 reference statements)

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“…Our group has developed a photocatalytic aerobic epoxidation mediated by tetramethylguanidine (TMG) (Figure 1e). 34 However, TMG exhibits toxicity and the reaction is slow. As far as we know, the reported metalfree methods using molecule oxygen as the oxidant were only suitable for the electron-poor olefins.…”

Section: ■ Introductionmentioning

confidence: 99%

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Sustainable and Practical Access to Epoxides: Metal-Free Aerobic Epoxidation of Olefins Mediated by Peroxy Radical Generated In Situ

Tang

Zhao

et al. 2019

ACS Sustainable Chem. Eng.

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A sustainable and practical protocol to prepare epoxides has been established by using air as the oxidant in the presence of K2CO3 in isopropylbenzene (CM) at 80–140 °C. The olefins are successfully converted into their corresponding epoxides in yields of up to 99%. CM and K2CO3 are reused in the scale-up recycling experiments. A reaction mechanism dominated by the radical pathway is proposed according to the control experiments and kinetic analysis.

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Section: ■ Introductionmentioning

confidence: 99%

“…2-Ethylanthrahydroquinone was reacted with O 2 to generate H 2 O 2 , which then reacted with olefins to yield epoxides (Figure b). Our group has developed a photocatalytic aerobic epoxidation mediated by tetramethylguanidine (TMG) (Figure e) . However, TMG exhibits toxicity and the reaction is slow.…”

Section: Introductionmentioning

confidence: 99%

Sustainable and Practical Access to Epoxides: Metal-Free Aerobic Epoxidation of Olefins Mediated by Peroxy Radical Generated In Situ

Tang

Zhao

et al. 2019

ACS Sustainable Chem. Eng.

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“…We synthesized (E)-N'-(substituted phenyl)-N,N-dimethyl formimidamides (2 a-e) by treating substituted anilines (1 a-e) with N,Ndimethylformamidine dimethyl acetal (CH(OMe) 2 NMe 2 ) in dry toluene under reflux condition. [24,25] We were also able to get the product using trimethyl orthoformate instead of DMF-DMA but in impure form. Compounds 2 a-e further stirred with hydroxylamine hydrochloride in dry methanol at room temperature for 2 h to afford the corresponding oximes (3 a-e) in good yields.…”

Section: Chemistrymentioning

confidence: 98%

Efficient Synthesis and Computational Studies of Useful Guanylating Agents: 1H‐Benzotriazole‐1‐carboximidamides

et al. 2020

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A new synthetic protocol for the synthesis of 1H-benzotriazole-1-carboximidamides starting from aryl amines in presence of acylbenzotriazole has been reported. The versatile guanylating agents could be an efficient synthetic tool for the synthesis of various guanidines. The present approach enables all possible variations of the substituents at different positions of the products. Single crystal of compound 4e was obtained by recrystallization from suitable solvent systems for X-ray and DFT studies. The reaction goes faster and yields more product with higher purity when Cbz protected aminoacyl benzotriazole used instead of aryl benzotriazole for the synthesis of the 1H-benzotriazole-1-carboximidamides. Computational studies were carried out to elucidate the energy profile and transition states to support the experimental data. Short reaction time, simple workup, high yields, and mild conditions are the key advantages of this protocol.

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“…Heterogeneous catalyst offers shorter reaction time, mild reaction conditions and high yields as compared to other homogeneous catalyst such as trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane (DHPDMDO), 1,1-dihydroperoxycyclohexane, UHP, H 2 O 2 , t-BuOOH [129]. Current metal-free approach aerobic photoepoxidation of chalcones have been reported by using amidies tetramethylguuanidine and tetraphenylporphine (H 2 TPP) to provide 32% yield of desired product [130].…”

Section: Other Catalystmentioning

confidence: 99%

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Farooq

Ngaini

2020

Chemistry Africa

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Epoxy chalcone is a heterocyclic molecule and an important precursor for the synthesis of biologically active compounds. This mini-review is elucidating the synthetic strategies of chalcone epoxide via one pot and two pot routes including nature of reactants, nature of catalyst and variety of catalyst to improve yield of desired product, biological applications and advantages and drawbacks of these synthetic strategies. One pot route has wide variety of reactants and efficient one is the condensation of aldehyde and ketone. However, two pot route is consisted of chalcone synthesis preceding to epoxy chalcone. The synthetic routes for the preparation of epoxy chalcone and the usage as a precursor for the synthesis of various organic molecules with biological application is comprehensively discussed. This review is outstanding in organic chemistry and pharmaceutical industries to produce new molecules with various applications. Graphic AbstractO O

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Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

Cited by 36 publications

References 121 publications

Sustainable and Practical Access to Epoxides: Metal-Free Aerobic Epoxidation of Olefins Mediated by Peroxy Radical Generated In Situ

Sustainable and Practical Access to Epoxides: Metal-Free Aerobic Epoxidation of Olefins Mediated by Peroxy Radical Generated In Situ

Efficient Synthesis and Computational Studies of Useful Guanylating Agents: 1H‐Benzotriazole‐1‐carboximidamides

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

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