Gold‐Catalysed Direct Couplings of Indoles and Pyrroles with 1,3‐Dicarbonyl Compounds

Arcadi, Antonio; Alfonsi, Maria; Bianchi, Gabriele; D’Anniballe, Gaetano; Marinelli, Fabio

doi:10.1002/adsc.200505345

Cited by 65 publications

(36 citation statements)

References 59 publications

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“…Metal activation of 1,3‐dicarbonyl compounds towards the reaction with indoles has been introduced ten years ago using Au III salts, and anhydrous FeCl 3 (Scheme ) . Linear 1,3‐diketones and β‐ketoesters as well as 1,3‐cycloakanediones can be used to afford the corresponding alkenylated indoles.…”

Section: Addition–elimination Of Indoles To Carbonyl Derivativesmentioning

confidence: 99%

“…Metal activation of 1,3-dicarbonyl compounds towards the reactionw ith indoles hasb een introduced ten years ago using Au III salts, [180] and anhydrous FeCl 3 (Scheme 90). [181] Linear1 ,3diketones and b-ketoesters as well as 1,3-cycloakanediones can be used to afford the corresponding alkenylated indoles.T he utilization of FeCl 3 as catalysts eems more effective than Au III derivatives but the latter metal shows ah igher versatility since the reaction can also be appliedt oatandemp rocess starting from remote precursorso ft he indole ring such as 2-alkynyl Scheme87.…”

Section: C-3 Alkenylationsmentioning

confidence: 99%

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Regioselective Direct C‐Alkenylation of Indoles

Petrini

2017

Chemistry A European J

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The direct introduction of alkenyl groups into the indole framework avoiding its preliminary functionalization can be carried out using different synthetic strategies. Transition-metal complexes facilitate the C-H activation of indoles or alkenes allowing an efficient Csp - Csp bond formation. The hydroindolation of alkynes catalyzed by the same metal complexes or various acidic promoters can also be pursued for the alkenylation process. Conjugate addition of electron-poor alkenes and direct condensation of carbonyl derivatives with indoles are also of interest for this purpose. The regiochemical control can be exploited using the intrinsic C-3 reactivity of the indole ring. The introduction of a suitable directing group at the nitrogen atom allows the preparation of C-2 alkenylated derivatives by transition metal catalyzed reactions. This review collects the fundamental contributions in this field reported in literature during the last fifteen years.

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Section: Addition–elimination Of Indoles To Carbonyl Derivativesmentioning

confidence: 99%

Section: C-3 Alkenylationsmentioning

confidence: 99%

Regioselective Direct C‐Alkenylation of Indoles

Petrini

2017

Chemistry A European J

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“…This latter pathway (Path A, Scheme ), involving a dual role of the catalyst as both π‐ and σ‐activator, was suggested to be more likely. In related experiments, application of gold(III) catalysis accomplished a sequential cyclization/alkenylation reaction of 2‐alkynylanilines with 1,3‐dicarbonyls (Scheme ) 53…”

Section: Gold‐catalyzed Sequential Reactions Of 2‐alkynylanilinesmentioning

confidence: 99%

Synthesis of Indole Derivatives from 2‐Alkynylanilines by Means of Gold Catalysis

Abbiati¹,

Marinelli

Rossi³

et al. 2013

Israel Journal of Chemistry

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The peculiar features of gold(III) and gold(I) species include exceptional carbophilicity and, at the same time, lone pair affinity. Such a combination offers many advantages for the development of more sustainable approaches to the synthesis of indole derivatives from readily available 2‐alkynylanilines. This mini‐review critically summarizes the literature reports in this field, with the aim to encourage further research activities in this promising area.

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“…Gold catalysts have also been used in domino sequences starting from o -alkynylanilines. Arcadi and Marinelli reported that gold-catalyzed cyclization of 2-alkynylanilines can be followed by 1,4-addition to enones [15–16], iodination [17] or reaction with 1,3-dicarbonyl compounds [18]. Perumal recently demonstrated that aldehydes and nitroalkenes can be used as electrophilic partners [19–20].…”

Section: Introductionmentioning

confidence: 99%

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

Brand

Chevalley

Waser³

2011

Beilstein J. Org. Chem.

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SummaryThe Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents).

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Gold‐Catalysed Direct Couplings of Indoles and Pyrroles with 1,3‐Dicarbonyl Compounds

Cited by 65 publications

References 59 publications

Regioselective Direct C‐Alkenylation of Indoles

Regioselective Direct C‐Alkenylation of Indoles

Synthesis of Indole Derivatives from 2‐Alkynylanilines by Means of Gold Catalysis

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

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