Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans

Liu, Jiupeng; Tang, Shuo; Wang, Shichong; Cao, Mengting; Zhao, Jingjing; Zhang, Puyu; Li, Pan

doi:10.1021/acs.joc.2c00989

Cited by 19 publications

(6 citation statements)

References 36 publications

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“…In the same year, a visible‐light‐induced 1,6‐enyne‐triggered C−Br bond homolysis of bromomalonates has been developed by the Zhao, Zhang, and Li group (Scheme 136). [110] This transition‐metal‐free, photocatalyst‐free, oxidant‐free, and additive‐free protocol afforded an approach for divergent synthesis of carbonylated and hydroxylated benzofurans in moderate to good yields under mild conditions with broad functional group tolerance. To prove the practicality of this transformation, some synthetic applications of functionalized benzofuran have been conducted.…”

Section: Visible‐light‐induced Cyclization Of 16‐enynesmentioning

confidence: 99%

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Liu,

Xu,

Han

et al. 2024

Adv Synth Catal

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Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products and biologically active pharmaceutical molecules. Over the past few decades, the development of novel and versatile synthetic approaches via cascade cyclization reactions of 1,6‐enynes for the construction of a series of fused and spiro compounds has been the focus of a great deal of research initiatives. These synthesis strategies are peculiarly fascinating in the context of the assembly of a wide array of pharmaceutical molecules, natural products, agrochemicals, and functional materials. In this review, recent developments in the transformations of 1,6‐enynes with diverse coupling reagents are summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed cyclization of 1,6‐enynes; 3) Metal‐free cyclization of 1,6‐enynes; 4) Visible‐light‐induced cyclization of 1,6‐enynes; 5) Electrocatalytic cyclization of 1,6‐enynes.

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Section: Visible‐light‐induced Cyclization Of 16‐enynesmentioning

confidence: 99%

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Liu,

Xu,

Han

et al. 2024

Adv Synth Catal

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“…[10] Among the most recent photo-mediated methodologies reported for their preparation in the last five years, in 2022, Liu, Tang et al developed a divergent synthesis of carbonylated 3 and hydroxylated benzofurans 4 via a metal-and catalyst-free radical annulation of 1,6-enynes 1 in the presence of bromomalonates 2 under irradiation at 405 nm (Scheme 1). [11] In this case, an energy transfer (ET) was exploited to generate alkyl and bromine radicals through the homolysis of the bond CÀ Br of bromomalonate 2, a rarely followed pathway. [12] The solvent played a crucial role for the divergence of the reaction allowing the carbonylated products 3 to be obtained in MeOH, while the hydroxylated benzofurans 4 were preferentially formed in non protic solvents such as toluene.…”

Section: Five-membered Ringsmentioning

confidence: 99%

Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst

Renzi,

Scarfiello,

Lanfranco

et al. 2023

Eur J Org Chem

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Achieving high molecular complexity can be not trivial, but the exploitation of domino reactions provides an atom‐ and step‐economical method to reach this target. Over the past decades, a lot of efforts have been put on the development of photocatalytic cascades employing both metal‐based and purely organic catalysts. Despite the effectiveness of these protocols, catalyst‐ and additive‐free light‐induced domino reactions are gaining momentum thank to their efficiency, operational simplicity and sustainability. The increasing number of papers published on this field in the last years is a proof of the appeal of these transformations. In this Review, we discuss domino and multicomponent reactions mediated by light with a focus on photocatalyst‐ and additive‐free processes. The most recent advances in the synthesis of complex nitrogen‐, oxygen‐, sulphur/selenium‐heterocycles together with multicomponent cascades are analysed with an emphasis on both experimental and mechanistic studies.

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“…Inspired by visible light-promoted carbene transfer reactions of diazoacetates, we wondered whether nitrilium ions could form in situ from nitriles and diazoacetates under visible light irradiation. Because of our ongoing interest in the transformations of diazo compounds and visible light-promoted reactions toward heterocyclic synthesis, we sought to develop a visible light-promoted direct N-imidoylation of benzotriazoles with diazoacetates and nitriles . To the best of our knowledge, metal-free generation of nitrilium ions from diazoacetates and nitriles is unprecedented.…”

mentioning

confidence: 99%

Visible Light-Promoted Diazoacetates and Nitriles Generating Nitrilium Ions Trapped by Benzotriazoles and Carboxylic Acids

et al. 2022

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A visible light-promoted generation of nitrilium ions from diazoacetates and nitriles has been developed. The reaction utilized visible light transformation of diazoacetates to the free carbene that could be trapped by nitriles to generate nitrilium ions, followed by nucleophilic attack on the benzotriazoles and carboxylic acids. This protocol provides an efficient and practical approach to N-imidoylbenzotriazoles and diacylglycine esters in good to excellent yields.

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Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans

Cited by 19 publications

References 36 publications

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst

Visible Light-Promoted Diazoacetates and Nitriles Generating Nitrilium Ions Trapped by Benzotriazoles and Carboxylic Acids

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