Gold‐Catalyzed Annulations of 1‐(2,3‐Butadienyl)‐1<i>H</i>‐Indole Derivatives

Barluenga, José; Piedrafita, María; Ballesteros, Alfredo; Suárez‐Sobrino, Ángel L.; González, José Manuel

doi:10.1002/chem.201001754

Cited by 53 publications

(32 citation statements)

References 98 publications

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“…However, when position 3 of indolylallene 1 contains an alkyl mild electron‐donating group, the complex undergoes 6‐ endo‐trig cyclisation with formation of the cyclic vinyl‐platinum intermediate D . Protodemetalation of these species would explain the formation of the non‐conjugated cyclic allyl indole 4 , analogous to that proposed by Barluenga et al . in the gold‐catalysed cyclisation.…”

Section: Resultssupporting

confidence: 70%

“…In order to clarify the involvement of cycles 4 x and 4 x′ as intermediates in the formation of the 2,3′‐BIMs and to get more evidence on the pathways involved in the reaction, we synthesised the non‐conjugated cycle 4 a via gold‐catalysed cyclisation of 3‐methyl‐ N‐ (2,3‐butadienyl)indole 1 a as reported by Barluenga et al . This molecule was submitted to platinum catalysis in the absence and presence of external indole …”

Section: Resultsmentioning

confidence: 99%

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Synthesis of a Novel Type of 2,3′‐BIMs via Platinum‐Catalysed Reaction of Indolylallenes with Indoles

Cooper

Alonso

Eagling

et al. 2018

Chemistry A European J

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Optimisation, scope and mechanism of the platinum‐catalysed addition of indoles to indolylallenes is reported here to give 2,3′‐BIMs with a novel core structure very relevant for pharmaceutical industry. The reaction is modulated by the electronic properties of the substituents on both indoles, with the 2,3′‐BIMs favoured when electron donating groups are present. Although simple at first, a complex mechanism has been uncovered that explains the different behaviour of these systems with platinum when compared with other metals (e.g. gold). Detailed labelling studies have shown Pt‐catalysed 6‐endo‐trig cyclisation of the indollylallene as the first step of the reaction and the involvement of two cyclic vinyl‐platinum intermediates in equilibrium through a platinum carbene, as the key intermediates of the catalytic cycle towards the second nucleophilic attack and formation of the BIMs.

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Section: Resultssupporting

confidence: 70%

Section: Resultsmentioning

confidence: 99%

Synthesis of a Novel Type of 2,3′‐BIMs via Platinum‐Catalysed Reaction of Indolylallenes with Indoles

Cooper

Alonso

Eagling

et al. 2018

Chemistry A European J

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“…[71,72] Thus, according to the method reported in the first of these works, hydroarylation of 2-allenylindoles 56, conducted in the presence of a chiral gold(I) catalyst, led to the synthesis of tetrahydrocarbazoles 57 with high enantiomeric control. Early reports on this topic were provided by Wiedenhöfer and by Barluenga, who studied the reactivity of 2-and N-allenylindoles, respectively (Scheme 22).…”

Section: Intramolecular Hydroarylation Of Allenesmentioning

confidence: 99%

Gold‐Catalyzed Functionalization Reactions of Indole

Pirovano

2018

Eur J Org Chem

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This review summarizes the progress achieved in the last fifteen years by application of homogeneous gold catalysis in the field of indole functionalization. Several electrophilic species obtained through gold‐catalyzed π‐activation have in fact been found to react with the nucleophilic positions of indole, thus allowing its efficient manipulation. In order to furnish a complete and clear overview on the role of the catalyst, the review is organized from the perspective of the gold‐activated substrate that is reacting with the indole. In addition, in view of the ability of gold to catalyze tandem and cascade reactions, a separate section describes tandem/cascade protocols useful for the synthesis of complex polycyclic indole derivatives. Finally, gold catalysis has also been employed for the synthesis of indole‐based natural products. For this reason, a dedicated section collects all the work in which the key step to obtain these complex indoles is represented by a gold‐catalyzed reaction.

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“…Further examples of gold-catalyzed cyclizations of allene-substituted indoles were presented by González and Widenhoefer, 15,16 as well as in the recent synthesis of flinderoles B and C by Toste et al, 17 which showed potent antimalarial activity. Zhang et al also utilized a cascade reaction catalyzed by both a gold catalysis and a protic acid as a key step in the total synthesis of dihydrocorynantheol 48 (Scheme 9) and the formal synthesis of yohimbines 49a and 49b.…”

Section: Cyclization-rearomatization Strategymentioning

confidence: 99%

Gold Approaches to Polycyclic Indole Alkaloids

et al. 2014

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Indole alkaloids are a highly diverse and ubiquitous family of natural products often identified in plants that have been used as traditional medicine for millennia. Because of their complex molecular architecture and relevance as potent pharmaceuticals, efficient methods for constructing these polycyclic skeletons are essential for their synthesis. Herein, we review recent developments in gold catalysis as a means toward the synthesis of many biologically important polycyclic indole alkaloids.

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Gold‐Catalyzed Annulations of 1‐(2,3‐Butadienyl)‐1H‐Indole Derivatives

Cited by 53 publications

References 98 publications

Synthesis of a Novel Type of 2,3′‐BIMs via Platinum‐Catalysed Reaction of Indolylallenes with Indoles

Synthesis of a Novel Type of 2,3′‐BIMs via Platinum‐Catalysed Reaction of Indolylallenes with Indoles

Gold‐Catalyzed Functionalization Reactions of Indole

Gold Approaches to Polycyclic Indole Alkaloids

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