Aerobic Oxidative Functionalization of Indoles

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(18), P. 3795 - 3823

Published: May 18, 2020

Abstract The synthetic methodology for direct indole functionalizations is of great significance in chemistry and has been intensively investigated the last few decades. From perspective green chemistry, oxygen best choice as terminal oxidant molecular synthesis. Hence, aerobic oxidative functionalization indoles became a hot research topic decade. Numerous efficient protocols this field have discovered that enable facile transformations to related valuable compounds, which are summarized discussed detail review. magnified image

Language: Английский

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Is Cu(iii) a necessary intermediate in Cu-mediated coupling reactions? A mechanistic point of view

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(49), P. 6609 - 6619

Published: Jan. 1, 2020

The mechanism of copper-mediated coupling reactions has aroused widespread interest, and it been found to not be as simple initially thought. In this article, we give an overview the recent advances in field. Notably, focus on whether presence CuIII is adopted catalytic cycle. Attention paid key CuII species, which can generated by radical-type or single electron transfer (SET) oxidation CuI. species oxidized SET using a nucleophilic radical for further reductive elimination. Alternatively, substitution bimetallic elimination avoid formation CuIII, also achieved.

Language: Английский

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Metal-free synthesis of indolo[2,3-b]indoles through aerobic cascade dehydrogenative aromatization/oxidative annulation

Green Synthesis and Catalysis, Journal Year: 2021, Volume and Issue: 2(1), P. 78 - 81

Published: Jan. 22, 2021

A convenient method for the rapid construction of indolo[2,3-b]indoles has been developed. This cascade reaction involving condensation, dehydroaromatization, and oxidative annulation was achieved in a one-pot TMSI/DMSO system, providing diversity functionalized satisfactory yields under facile metal-free conditions. The present protocol provides straightforward approach to access structurally valuable indolo[2,3-b], indoles.

Language: Английский

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One-electron oxidative dehydrogenative annulation and cyclization reactions

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(15), P. 2107 - 2144

Published: Jan. 1, 2020

This review focuses on the recent advances in one-electron oxidation involved oxidative dehydrogenative annulations and cyclizations for intermolecular intramolecular construction of valuable ring structures.

Language: Английский

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Copper–iodine co-catalyzed C–H aminoalkenylation of indoles via temperature-controlled selectivity switch: facile synthesis of 2-azolyl-3-alkenylindoles

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(14), P. 3794 - 3799

Published: Jan. 1, 2022

An efficient copper–iodine co-catalyzed 2,3-difunctionalization of indoles with azoles and phenols via temperature-controlled selectivity switch has been developed for the green synthesis 2-azolyl-3-alkenylindoles.

Language: Английский

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Chemodivergent Synthesis of Indeno[1,2-b]indoles and Isoindolo[2,1-a]indoles via Mn(III)-Mediated or Electrochemical Intramolecular Radical Cross-Dehydrogenative Coupling

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(16), P. 10967 - 10981

Published: July 28, 2022

Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials involving radical cross-dehydrogenative couplings have been developed. Mn(OAc)3·2H2O selectively promoted an intramolecular C–H/C–H dehydrogenative coupling reaction to provide indeno[1,2-b]indoles, while C–H/N–H could proceed via electrochemistry deliver isoindolo[2,1-a]indoles. Plausible mechanisms chemodivergent reactions were proposed.

Language: Английский

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Iron–iodine co-catalysis towards tandem C–N/C–C bond formation: one-pot regioselective synthesis of 2-amino-3-alkylindoles

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6165 - 6171

Published: Jan. 1, 2022

An efficient intermolecular C2,3-H aminoalkylation of indoles with 9 H -xanthenes and azoles via iron–iodine co-catalyzed tandem C–N/C–C bond formation has been developed.

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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Iridium/Acid Cocatalyzed Direct Access to Fused Indoles via Transfer Hydrogenative Annulation of Quinolines and 1,2-Diketones

Organic Letters, Journal Year: 2020, Volume and Issue: 22(6), P. 2308 - 2312

Published: Feb. 28, 2020

Herein, we present an unprecedented iridium/acid cocatalyzed construction of fused indoles via transfer hydrogenative annulation nonactivated quinolines and 1,2-diketones. The products are assembled initial reduction followed by selective coupling 1,2-diketones with the N C8 sites quinolyl skeleton. developed synthetic method features operational simplicity, readily available feedstocks, applicability for streamline synthesis functional molecules, high step atom efficiency, generation water as byproduct.

Language: Английский

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Recent Advances towards the Synthesis and Material Applications of Indoloindoles

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(16)

Published: June 2, 2022

Abstract An important class of N ‐heteroacenes is indoloindoles which are air‐stable, electron‐rich and possess many tuneable properties. Initially, were explored for potential biological applications but current interest based on their performance as photovoltaic materials. With growing across multiple facets organic functional materials, the need efficient methods to synthesize functionalize has taken a centre stage. Over years, synthetic routes leading have evolved from multistep protocols one‐pot multicomponent synthesis. Present literature boasts variety reports that employ metals such Cu, Ru, Rh, Pd, or Au mediate reaction towards indoloindoles. As alternatives metal‐mediated methods, researchers also developed metal‐free catalyst‐free conditions. Indoloindoles, fundamentally fused‐indoles, often synthesized by transforming indole derivatives anilines arynes starting substrates equally abundant. The present review highlights rich diversity versatility recent synthesis indolo[3,2‐ b ]indoles, indolo[2,3‐ indolo[7,6‐ g indolo[5,4‐ e ]indoles. This discusses explicitly designed obtain above‐mentioned explores several other can be adapted access said heteroacenes. Available mechanistic details pertaining novel transformations been detailed readers. Various where function light‐emitting diodes, field‐effect transistors, solar cells, etc. delved into before concluding with an outlook future research.

Language: Английский

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