Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation

Organic Letters, Год журнала: 2021, Номер 23(11), С. 4109 - 4114

Опубликована: Май 14, 2021

We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to series aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that occurs under sole light irradiation without need for exogenous photoredox catalysts. More significantly, reasonable mechanism was proposed on basis control experiments density functional theory calculation results.

Язык: Английский

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Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate

Chinese Journal of Organic Chemistry, Год журнала: 2021, Номер 41(12), С. 4565 - 4565

Опубликована: Янв. 1, 2021

Carbene is one of the most important synthetic intermediates in organic synthesis.In past few decades, transition-metal catalyzed carbene transfer reactions have made remarkable development.Recently, visible light-promoted transformation diazo compounds through formation free as key intermediate begun to rise.The reaction only need light sole energy source which meets concept green chemistry.Since pioneering works developed by groups Diaves and Zhou, photo-promoted has attracted more attentions.On basis previous work, latest progress this field further improved, mainly focuses on recent new under irradiation contributions reported from Chinese research group.The future development direction, well challenges prospected.

Язык: Английский

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Oxime Ether Synthesis through O–H Functionalization of Oximes with Diazo Esters under Blue LED Irradiation

Organic Letters, Год журнала: 2021, Номер 23(17), С. 6951 - 6955

Опубликована: Авг. 12, 2021

A green and sustainable oxime ether formation method via the visible-light-promoted O–H functionalization of oximes with diazo esters is described. The reaction occurs under very mild conditions (catalyst- additive-free) a high yield functional group tolerance. When was performed cyclic as solvent (e.g., THF, 1,4-dioxane, tetrahydropyran, ect.), an interesting photochemical three-component product obtained in good yields.

Язык: Английский

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Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes

Chemical Science, Год журнала: 2022, Номер 13(11), С. 3273 - 3280

Опубликована: Янв. 1, 2022

Visible light induced singlet nucleophilic carbenes undergo rapid [2 + 1]-cycloaddition with tethered olefins to afford unique bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane scaffolds. This cyclopropanation process requires only visible irradiation proceed, circumventing the use of exogenous (photo)catalysts, sensitisers or additives showcases a vastly underexplored mode reactivity for in chemical synthesis. The discovery additional transformations including cyclopropanation/retro-Michael/Michael cascade chromanones photochemical C-H insertion reaction are also described.

Язык: Английский

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Visible-light-driven multicomponent reactions to access S-alkyl phosphorothioates using elemental sulfur as the sulfur source

Green Chemistry, Год журнала: 2022, Номер 24(12), С. 4915 - 4920

Опубликована: Янв. 1, 2022

A convenient and eco-friendly visible-light promoted multicomponent protocol has been developed for the synthesis of S -alkyl phosphorothioates by using elemental sulfur as cheap odorless source.

Язык: Английский

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Visible-Light-Mediated Formal Carbene Insertion Reaction: Enantioselective Synthesis of 1,4-Dicarbonyl Compounds Containing All-Carbon Quaternary Stereocenter

ACS Catalysis, Год журнала: 2022, Номер 12(9), С. 5510 - 5516

Опубликована: Апрель 25, 2022

We developed an efficient visible-light-mediated formal carbene insertion reaction of 1,3-diketones with diazoesters for the construction enantioenriched 1,4-dicarbonyl compounds a quaternary carbon center. Combining visible light and Brønsted acid catalyst, chiral were achieved in good yields high enantioselectivities by photochemical transfer protocol.

Язык: Английский

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Visible Light‐Mediated Cyclopropanation: Recent Progress

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(44)

Опубликована: Окт. 21, 2022

Abstract Cyclopropanes are one of the most important strained rings existing in various pharmaceutical products and secondary metabolites. They also widely used total synthesis natural products, medicinal chemistry, materials science. In past years, photochemical cyclopropanation has been gradually developed as a robust attractive synthetic method to prepare diverse cyclopropane backbones. this review, we summarize recent advances visible light‐mediated synthesis, especially using carbene transfer strategy photocatalytic radical reactions.

Язык: Английский

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Visible-Light-Mediated Energy Transfer Enables Cyclopropanes Bearing Contiguous All-Carbon Quaternary Centers

ACS Catalysis, Год журнала: 2023, Номер 13(14), С. 9806 - 9816

Опубликована: Июль 11, 2023

Cyclopropanes bearing contiguous all-carbon quaternary centers continue to attract attention due their bioactivities. However, methods obtain cyclopropanes with remain largely unexplored the high steric hindrance of these compounds. Herein, we report a visible-light-mediated energy-transfer (EnT) strategy realize in situ donor/donor carbenes from readily available N-tosylhydrazones, facilitating synthesis highly congested EWG-free cyclopropanes. Through this approach, are rapidly installed into complex bioactive molecules, fluorescent and other useful building blocks that challenging synthesize. Detailed mechanistic reactions DFT studies clearly demonstrated role photosensitizer, formation carbenes, necessity light base system.

Язык: Английский

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A Spiro Phosphamide Catalyzed Enantioselective Proton Transfer of Ylides in a Free Carbene Insertion into N−H Bonds

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(15)

Опубликована: Фев. 14, 2023

Free carbene readily causes multiple side reactions due to its high energy, thus asymmetric transformation is very difficult. We present here our findings of high-pKa Brønsted acid catalysts that enable free insertion into N-H bonds amines prepare chiral α-amino derivatives with enantioselectivity. Under irradiation visible light, diazo compounds produce high-energy carbenes are captured by form ylide intermediates, and then the newly designed acids, spiro phosphamides, promote proton transfer ylides afford products. Computational kinetic studies uncover principle for rational design proton-transfer explain how accelerate this provide stereocontrol.

Язык: Английский

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Visible photons as ideal reagents for the activation of coloured organic compounds

Chemical Society Reviews, Год журнала: 2024, Номер 53(10), С. 4926 - 4975

Опубликована: Янв. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Язык: Английский

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