Transition-metal-catalyzed site-selective C7-functionalization of indoles: advancement and future prospects

Chemical Communications, Journal Year: 2018, Volume and Issue: 55(5), P. 572 - 587

Published: Dec. 5, 2018

C7-Decorated indoles are important structural motifs present in a plethora of bioactive and pharmaceutical compounds. Early stage developments for C7 modifications were realized through directed metallation (DOM) subsequent quenching with suitable electrophiles or by halogenation Cu(ii) halides. Direct C-7 functionalization is comparatively difficult compared to at C-2 C-3 positions owing the inherent reactivity pyrrole-type ring. However, recently transition-metal-catalyzed auxiliary assisted site-selective has emerged as an elegant synthetic tool carbon-carbon carbon-heteroatom bond formation diversify indoles. This article covers advancement, application mechanistic underpinnings evolved transformations otherwise inert C7-H up October 2018.

Language: Английский

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Synthesis of Fused or Spiro Polyheterocyclic Compounds via the Dehydrogenative Annulation Reactions of 2-Arylindazoles with Maleimides

Organic Letters, Journal Year: 2019, Volume and Issue: 21(18), P. 7189 - 7193

Published: Sept. 4, 2019

A dehydrogenative annulation of 2-arylindazoles with maleimides for the switchable synthesis indazolo[2,3-a]pyrrolo[3,4-c]quinolinones or spiroindolo[1,2-b]indazole-11,3′-pyrrolidinones is presented. Mechanistically, formation title compounds involves a Rh(III)-catalyzed C–H metalation 2-arylindazole, followed by maleimide insertion and intramolecular cyclization. Interestingly, selectivity to form fused spiro could be switched resorting different additives. The notable features this protocol include simple substrates excellent atom economy regioselectivity.

Language: Английский

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Mechanochemical Solvent‐Free Catalytic C−H Methylation

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(12), P. 6660 - 6666

Published: Oct. 8, 2020

The mechanochemical, solvent-free, highly regioselective, rhodium-catalyzed C-H methylation of (hetero)arenes is reported. reaction shows excellent functional-group compatibility and demonstrated to work for the late-stage biologically active compounds. method requires no external heating benefits from considerably shorter times than previous solution-based protocols. Additionally, mechanochemical approach shown enable efficient synthesis organometallic complexes that are difficult generate conventionally.

Language: Английский

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Transition metal-catalyzed coupling of heterocyclic alkenesviaC–H functionalization: recent trends and applications

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(12), P. 1527 - 1569

Published: Jan. 1, 2020

Heterocyclic alkenes and their derivatives are an important class of reactive feedstock valuable synthons. This review highlights the transition-metal-catalyzed coupling heterocyclic alkenesviaa C–H functionalization strategy.

Language: Английский

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Cobalt(III)-Catalyzed [4 + 2] Annulation of N-Chlorobenzamides with Maleimides

Organic Letters, Journal Year: 2019, Volume and Issue: 21(4), P. 1068 - 1072

Published: Jan. 28, 2019

A Co(III)-catalyzed novel [4 + 2] annulation of N-chlorobenzamides with maleimides has been reported. Mostly, are known to furnish the Michael-type or 1,1-type cyclized products while treating amides. In this reaction, furnished annulated in good yields at room temperature being treated internal oxidizing N-chlorobenzamide as a directing group. The developed methodology is compatible variety functional groups. obtained featured some biologically active molecules.

Language: Английский

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Aerobic Oxidative Alkenylation of Weak O-Coordinating Arylacetamides with Alkenes via a Rh(III)-Catalyzed C–H Activation

Organic Letters, Journal Year: 2019, Volume and Issue: 21(5), P. 1320 - 1324

Published: Feb. 14, 2019

A versatile and site-selective rhodium(III)-catalyzed aerobic oxidative alkenylation of arylacetamides including primary, secondary, tertiary amides having a weak O-coordinating acetamide directing group with alkenes is described. In the reaction, air was utilized as sole oxidant. The reaction compatible activated maleimides.

Language: Английский

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Cp*Co^III–Catalyzed Alkylation of Primary and Secondary C(sp³)-H Bonds of 8-Alkylquinolines with Maleimides

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(3), P. 1542 - 1552

Published: Jan. 8, 2019

The cobalt(III)-catalyzed C(sp3)-H bond alkylation of 8-methyl quinoline with maleimides is reported. In contrast to the rhodium-catalyzed method, in current cobalt-catalyzed a catalytic amount acid used, and importantly, it also applicable secondary alkylation. developed methodology for N-alkyl- N-aryl-substituted unsubstituted maleimides, tolerates variety functional groups on moiety. Atom-economy high regioselectivity good excellent yields alkylated products under mild reaction conditions are important features this method.

Language: Английский

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Recent Advances in Metal‐catalyzed Alkylation, Alkenylation and Alkynylation of Indole/indoline Benzenoid Nucleus

Chemistry - An Asian Journal, Journal Year: 2020, Volume and Issue: 15(24), P. 4184 - 4198

Published: Nov. 9, 2020

Selective editing of the benzenoid C-H bonds (C4-C7) in indoles/indolines has received great interest because functionalized are featured many marketed drugs and natural products. Transition-metal-catalyzed directed functionalization thus been developed to manipulate core through C-C C-heteroatom bond formation. This review covers recent advances selective forming reactions, alkylation, alkenylation alkynylation, over ring using metal catalysis.

Language: Английский

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Synthesis of maleimide fused benzocarbazoles and imidazo[1,2-a]pyridines via rhodium(iii)-catalyzed [4 + 2] oxidative cycloaddition

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(22), P. 3698 - 3704

Published: Jan. 1, 2020

In this paper, an efficient and sustainable synthesis of maleimide-fused benzocarbazoles/imidazo[1,2-a]pyridines from the reaction 2-arylindoles/2-arylimidazo[1,2-a]pyridines with maleimides through oxidative [4 + 2] annulation is presented.

Language: Английский

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Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(43), P. 5862 - 5879

Published: Oct. 20, 2021

Abstract Maleimides and succinimides are all vital scaffolds in biological fields various natural products. Maleimide derivatives have been extensively used as coupling partners for organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, variety efficient chelation‐assisted strategies employed selective addition C−H bonds to maleimides giving succinimides, which also highly building blocks synthesis. This Review provides an overview research progress relating participated transition‐metal‐catalyzed group‐directed alkylation from 2012 2021. Significant advances this field were highlighted, diverse transition metal catalysts, substrates contained different directing groups, reaction mechanisms well synthetic applications systematically discussed. addition, limitations intractable issues need be solved future pointed out.

Language: Английский

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