Synthesis of Polysubstituted Pyrroles via Silver-Catalyzed Oxidative Radical Addition of Cyclopropanols to Imines

Zhou, Yulu; Wu, Ming‐Chang; Liu, Yi; Cheng, Cungui; Zhu, Gangguo

doi:10.1021/acs.orglett.0c02735

Cited by 19 publications

(8 citation statements)

References 68 publications

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“…In 2020, a radical [3 + 2] cycloaddition reaction between cyclopropanols and imines for the preparation of polysubstituted pyrroles was reported by Zho et al [65] Among examining various silver salts, including AgNO 3 , AgOAc, Ag 2 CO 3 , AgBF 4 , and AgO 2 CCF 3 , control experiments showed that AgO 2 CCF 3 in the presence of Na 2 S 2 O 8 is the better catalyst for the cycloaddition reaction. Synthesis of N-aryl-pyrazoles through ringopening of cyclopropanols was developed by two research groups.…”

Section: Ring-opening Cyclization Reaction Of Cyclopropanolsmentioning

confidence: 99%

Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds

Doraghi,

Pegah Aledavoud,

Fakhrioliaei

et al. 2023

ChemistrySelect

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Cyclopropanols, due to their particular chemistry, can participate in various synthetic reactions with retention or cleavage of the strained three‐membered ring. Direct cross‐coupling ring‐opening reaction of such molecules access to organic compounds, such as ketones has great importance in medicinal chemistry and material sciences. Hence, the coupling reaction/cyclization ring‐opening of cyclopropanols for constructing new valuable molecules in the presence of a transition metal catalyst or under metal‐free conditions is described in this context. The features of the reactions are discussed, and the mechanisms of the challenging reactions are highlighted.

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Section: Ring-opening Cyclization Reaction Of Cyclopropanolsmentioning

confidence: 99%

Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds

Doraghi,

Pegah Aledavoud,

Fakhrioliaei

et al. 2023

ChemistrySelect

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show abstract

“…The latter process is challenging due to the relatively strong OÀ H bond (typical BDE values 103-105 kcal mol À 1 ). [4] The traditional methods for the generation of radicals A with the subsequent addition to double bonds of olefins require strong oxidative conditions provided by stoichiometric oxidants [5] and/or transition metal derivatives (Ag(I), [6][7][8] Fe(III), [9][10][11] Mn(III) [12][13][14] ) and elevated temperatures. [5,6,10,11,14] Currently, photoredox catalysis offers a number of bypassing strategies that allow the generation of ketoalkyl radicals from cyclopropanols [15,16] and even unstrained cycloalkanols under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

Ring‐Opening Coupling Reaction of Cyclopropanols with Electrophilic Alkenes Enabled by Decatungstate as Photoredox Catalyst

Krech,

Yakimchyk,

Jarg

et al. 2023

Adv Synth Catal

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We introduce a methodology for the photocatalytic generation of β‐ketoalkyl radicals from tertiary cyclopropanols, utilizing tetrabutylammonium decatungstate (TBADT) as a photoredox catalyst. The application is demonstrated by the synthesis of distantly functionalized ketones via the redox‐neutral addition of the cyclopropanol‐derived β‐ketoalkyl radicals to the double bond of electrophilic olefins. The transformation occurs under ambient temperature conditions and is suitable for coupling a wide range of cyclopropanol and alkene substrates. This was demonstrated by the preparation of 33 ketone products with 35–92% yield. The method's preparative robustness has been validated through upscaled preparations conducted under continuous flow conditions. Mechanistic investigations support the role of TBADT as a photoredox catalyst, which facilitates the single electron oxidation of cyclopropanols, followed by the electron transfer from the reduced form of decatungstate to the electrophilic double bond of alkene. Moreover, we found that electron‐rich aromatic cyclopropanols and electron‐deficient olefins form photoactive electron donor‐acceptor (EDA) complexes. This property allows the reaction to proceed under UV light irradiation via the photoinduced charge transfer in the absence of the photocatalyst.

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“…Xiong et al developed an efficient protocol for the synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerization [18]. In 2020, Zhu described direct synthesis of polysubstituted pyrroles via an Ag‐catalyzed formal [3 + 2] cycloaddition reaction [19]. Recently, De Sarkar et al reported an efficient electrochemical method for the synthesis of polysubstituted pyrroles [20].…”

Section: Introductionmentioning

confidence: 99%

Catalyst‐free one‐pot three‐component rapid synthesis of polysubstituted pyrroles by liquid‐assisted grinding

Jiang

Yan

Dong

et al. 2022

Journal of Heterocyclic Chem

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A series of polysubstituted pyrroles were rapidly synthesized in moderate to good yields via catalyst‐free one‐pot three‐component reaction of 1,3‐dicarbonyl compounds with primary amines and nitrostyrenes by using liquid‐assisted grinding. This protocol provides several advantages over the conventional chemical synthesis, such as simple work‐up procedure, wide substrate scope, short reaction time, and environmental friendliness. Structures of polysubstituted pyrroles were confirmed by 1H NMR, 13C NMR, and ESI‐MS studies.

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Synthesis of Polysubstituted Pyrroles via Silver-Catalyzed Oxidative Radical Addition of Cyclopropanols to Imines

Cited by 19 publications

References 68 publications

Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds

Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds

Ring‐Opening Coupling Reaction of Cyclopropanols with Electrophilic Alkenes Enabled by Decatungstate as Photoredox Catalyst

Catalyst‐free one‐pot three‐component rapid synthesis of polysubstituted pyrroles by liquid‐assisted grinding

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