Iron-Catalyzed Friedel–Crafts-type 3,5-Diacylation of Indoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10272 - 10282

Published: July 5, 2024

The exploration of remote functionalization indoles is impeded by the inherently dominant reactivity intrinsic to pyrrole moiety. Herein, we delineate a novel strategy facilitated Lewis acid mediation, enabling C-H functionalization, which culminates in synthesis an array selectively functionalized indole derivatives, encompassing 3-trifluoroacetyl and 5-benzoyl motifs, utilizing trifluoroacetic anhydride various acyl chlorides. Notably, protocol exhibits versatility, as epitomized extension C5-acylation alkylation sulfonation reactions. This methodology distinguished its exemplary regio- chemo-selectivity, extensive substrate scope, commendable tolerance diverse functional groups, employment comparatively mild reaction conditions.

Language: Английский

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5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds

Molecules, Journal Year: 2025, Volume and Issue: 30(2), P. 381 - 381

Published: Jan. 17, 2025

A Cu-promoted highly chemoselective dimerization of 5-aminopyrazoles to produce pyrazole-fused pyridazines and pyrazines is reported. The protocol generates switchable products via the direct coupling C-H/N-H, C-H/C-H N-H/N-H bonds, with merits broad substrate scope high functional group compatibility. Gram-scale experiments demonstrated potential applications this reaction. Moreover, preliminary fluorescence results uncovered that dipyrazole-fused may have some in materials chemistry.

Language: Английский

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One-pot Multicomponent Tandem Reaction for the Rapid Synthesis of 2-Amino-3-benzylindoles

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel one-pot oxidative cross-dehydrogenation coupling (CDC) reaction has been developed for the selective construction of C–N and C–C bonds at C2,3-positions indoles.

Language: Английский

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Recent Advances in Photo-promoted Generalized C3-H Alkylation of Quinoxalin-2(1H)-ones

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Recent advances in the photo-promoted C3–H alkylation reaction of quinoxalin-2(1 H )-ones with different agents.

Language: Английский

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Solvent-controlled switchable multicomponent tandem oxidative triple functionalization of indolines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1933 - 1940

Published: Jan. 1, 2024

A new one-pot method for solvent-controlled switchable tandem oxidative triple functionalization of indolines has been developed via successive regioselective chalcogenation, oxidation, amination and halogenation.

Language: Английский

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Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7216 - 7224

Published: May 2, 2024

An organoselenium-catalyzed C2,3-diarylation of unprotected N–H indoles with electron-rich aromatics has been developed. This one-pot multicomponent tandem cross-dehydrogenation coupling reaction allows for the incorporation two different aromatic groups to indoles. More importantly, this approach offers significant advantages, including a high atom and step economy, eliminating need prepreparation substrates, streamlining synthetic process enhancing its practicality. Overall, presents an efficient versatile strategy functionalization indole derivatives.

Language: Английский

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Directing-group-free strategy for the iodine-mediated regioselective dichalcogenation of indolines: understanding the full catalytic cycles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 871 - 884

Published: Dec. 11, 2023

A metal-free catalytic method for the regioselective direct dehydrogenation–dichalcogenation of indolines. The reaction mechanism and regioselectivity have been elucidated via density functional theory studies.

Language: Английский

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The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C₁₇H₁₂FN₃O

Zeitschrift für Kristallographie - New Crystal Structures, Journal Year: 2024, Volume and Issue: 239(5), P. 923 - 925

Published: July 31, 2024

Abstract C 17 H 12 FN 3 O, orthorhombic, Pbca (no. 61), a = 14.7608(7) Å, b 7.2802(4) c 24.4842(13) V 2,631.1(2) Å , Z 8, R gt ( F ) 0.0900, wR ref 2 0.1841, T 170 K.

Language: Английский

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Strategies Employing Transition‐Metal Free Conditions for C−C Bond Formation in Indoles

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(36)

Published: Sept. 19, 2024

Abstract Indole motifs are omnipresent in nature and can be found many natural products as well pharmaceuticals. It is for this reason synthetic transformations of indole have become a topic interest the organic medicinal chemist community decades. In review, we emphasized functionalization indoles via transition‐metal‐free approaches. This review touches on aspects different sub‐sections, which gives proposition tactics employed an overview road ahead.

Language: Английский

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