B(C6F5)3-Catalyzed α,β-Difunctionalization and C–N Bond Cleavage of Saturated Amines with Benzo[c]isoxazoles: Access to Quinoline Derivatives

He, Yan; Liu, Qimeng; Du, Zihe; Xu, Yanhua; Cao, Lingyu; Zhang, Xinying; Fan, Xuesen

doi:10.1021/acs.joc.2c01290

Cited by 8 publications

(2 citation statements)

References 51 publications

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“…In 2022, He, Fan and coworkers reported an α,β-functionalization strategy of anilines 102 with benzo[c]isoxazoles 103 followed by a C-N bond cleavage to furnish functionalized quinoline derivatives 104 (Scheme 13). 28 The catalytic cycle proceeds via B(C6F5)3-mediated abstraction of the α-N C(sp…”

Section: Template For Synlett Thiemementioning

confidence: 99%

“…In 2022, He, Fan and co-workers reported an ,-functionalization strategy involving anilines 102 and benzo[c]isoxazoles 103 followed by a C-N bond cleavage to furnish functionalized quinoline derivatives 104 (Scheme 13). 28 The catalytic cycle proceeds via B(C 6 The reaction tolerated a broad range of functional groups on the aniline 102 ring including cyano (e.g., 104a), trifluoromethyl, nitro, ether and thioether groups. The saturated heterocycle in 102 was varied to allow for pyrrolidines, piperidines, azepanes (e.g., 104b), and even azocanes and azonanes to all be used in the protocol.…”

Section: Cluster Account Synlettmentioning

confidence: 99%

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Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction

Elsherbeni

Winfrey

Lei

et al. 2023

Synlett

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C‒H functionalization is widely regarded as an important area in the development of synthetic methodology, enabling the design of more time- and atom-efficient syntheses. The ability of electron-deficient organoboranes to mediate hydride abstraction from α-amino C‒H bonds is therefore of great interest, as the reactive iminium and hydridoborate moieties generated are able to participate in a range of synthetically useful transformations. In this review update, we cover the recent advances made in organoborane mediated hydride abstraction, with particular focus on the catalytic applications of electron deficient boranes for α- or β- functionalization, α,β-difunctionalization, and the dehydrogenation of amines.

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Section: Template For Synlett Thiemementioning

confidence: 99%

Section: Cluster Account Synlettmentioning

confidence: 99%

Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction

Elsherbeni

Winfrey

Lei

et al. 2023

Synlett

View full text Add to dashboard Cite

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Rhodium-Catalyzed [4 + 2]-Annulation of o-Acylanilines with N-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines

2023

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Efficient synthesis of 3-aminoquinolines has been demonstrated from readily accessible N-sulfonyl-1,2,3-triazoles and oacylaniline derivatives. This transformation involves the generation of C−C and C−N bonds through insertion of rhodium azavinyl carbenoid into a N−H bond followed by cyclization and aromatization. The important features include good functional group tolerance, synthesis of indoloquinoline, and isolation of N−H-inserted product, a potential intermediate.

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Accessing Highly Substituted Indoles via B(C₆F₅)₃-Catalyzed Secondary Alkyl Group Transfer

Elsherbeni,

Melen,

Pulis

et al. 2024

J. Org. Chem.

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Herein, we report a synthetic method to access a range of highly substituted indoles via the B(C 6 F 5 ) 3 -catalyzed transfer of 2°alkyl groups from amines. The transition-metal-free catalytic approach has been demonstrated across a broad range of indoles and amine 2°alkyl donors, including various substituents on both reacting components, to access useful C(3)-alkylated indole products. The alkyl transfer process can be performed using Schlenk line techniques in combination with commercially available B(C 6 F 5 ) 3 •nH 2 O and solvents, which obviates the requirement for specialized equipment (e.g., glovebox). I ndole-containing molecules have diverse applications, spanning functional materials, pigments, and pharmaceuticals. 1 As such, the development of methods to access indoles with various substitution patterns has received considerable attention from the synthetic community. 2 Highly substituted indole frameworks, for example those bearing substitution at the 1-, 2-, and 3-positions, occur within biologically active molecules such as beclabuvir (antiviral drug for the treatment of hepatitis C virus (HCV) infection), deleobuvir (nonnucleoside inhibitor of HCV NS5B RNA polymerase), and bazedoxifene (selective estrogen receptor modulator) (Scheme 1). Despite their importance, relatively few methods exist for their synthesis, especially for those that contain 2°alkyl groups at the C(3)-position, which are typically accessed via C(3)alkylation of 1,2-disubstituted indoles. 3−7 Using 1,2-dimethylindole as a representative example, existing synthetic approaches include the Pt-catalyzed hydroarylation with styrene, reported in 2006 by Widenhoefer and co-workers, 3 which produced the corresponding C(3)-alkylated indole in 55% yield as a (1:1.1) mixture of linear and branched isomers (Scheme 2A). In 2011, Tsuchimoto and co-workers disclosed an In-catalyzed reductive alkylation protocol employing phenylacetylene and Ph 2 MeSiH as the reductant, which

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B(C₆F₅)₃-Catalyzed α,β-Difunctionalization and C–N Bond Cleavage of Saturated Amines with Benzo[c]isoxazoles: Access to Quinoline Derivatives

Cited by 8 publications

References 51 publications

Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction

Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction

Rhodium-Catalyzed [4 + 2]-Annulation of o-Acylanilines with N-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines

Accessing Highly Substituted Indoles via B(C₆F₅)₃-Catalyzed Secondary Alkyl Group Transfer

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B(C6F5)3-Catalyzed α,β-Difunctionalization and C–N Bond Cleavage of Saturated Amines with Benzo[c]isoxazoles: Access to Quinoline Derivatives

Cited by 8 publications

References 51 publications

Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction

Recent Advances in Catalysis Using Organoborane-Mediated Hydride Abstraction

Rhodium-Catalyzed [4 + 2]-Annulation of o-Acylanilines with N-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines

Accessing Highly Substituted Indoles via B(C6F5)3-Catalyzed Secondary Alkyl Group Transfer

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Product

Resources

About

B(C₆F₅)₃-Catalyzed α,β-Difunctionalization and C–N Bond Cleavage of Saturated Amines with Benzo[c]isoxazoles: Access to Quinoline Derivatives

Accessing Highly Substituted Indoles via B(C₆F₅)₃-Catalyzed Secondary Alkyl Group Transfer