Indium(III) bromide-catalyzed hydroarylation of alkynes with indoles

Bhaskar, G.; Saikumar, C.; Perumal, Paramasivan T.

doi:10.1016/j.tetlet.2010.04.036

Cited by 38 publications

(14 citation statements)

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“…In fact, catalysis by indium bromide, in particular, and indium salts, in general, has recently being recognized as an efficient method for the alkenylation of indoles with alkynes , . In our opinion, the glycal double bond in the postulated intermediate 39 , plays a key role facilitating the approach of the indole moiety towards the alkyne in the Friedel–Crafts process.…”

Section: Resultsmentioning

confidence: 97%

“…In our opinion, the glycal double bond in the postulated intermediate 39 , plays a key role facilitating the approach of the indole moiety towards the alkyne in the Friedel–Crafts process. Accordingly, in this transformation InBr 3 plays a key dual role by i) triggering the Ferrier rearrangement, and ii) facilitating the hydroarylation of the alkyne with indole …”

Section: Resultsmentioning

confidence: 99%

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Diversity‐Oriented Synthetic Endeavors of Newly Designed Ferrier and Ferrier‐Nicholas Systems Derived from 1‐C‐Alkynyl‐2‐deoxy‐2‐C‐Methylene Pyranosides

2018

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Novel pyranose derivatives that display Ferrier‐ and Ferrier‐Nicholas‐like reactivity have been designed. These systems: 1‐C‐alkynyl‐2‐deoxy‐2‐C‐methylene pyranosides (Ferrier), and their corresponding dicobalthexacarbonyl alkenyl derivatives (Ferrier‐Nicholas), which can be accessed by a concise synthetic route from commercially available tri‐O‐acetyl‐d‐glucal, allow the incorporation of two nucleophiles (at positions C‐3 and C‐2′) in the pyranose ring. The study of these systems has resulted in the discovery of novel reaction patterns that allow, among others, access to open‐chain derivatives, branched pyranosides, 1,6‐anhydro derivatives and, when reacting with indole, access to a new family of tetracyclic indole‐containing carbohydrate derivatives, namely, cyclohepta[b]indole‐fused glycals. The latter are, most likely, formed by a bis Ferrier‐type rearrangement followed by an unusual intramolecular 7‐endo‐dig Friedel–Crafts alkenylation of one of the indole moieties by the C‐1 alkyne.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Diversity‐Oriented Synthetic Endeavors of Newly Designed Ferrier and Ferrier‐Nicholas Systems Derived from 1‐C‐Alkynyl‐2‐deoxy‐2‐C‐Methylene Pyranosides

2018

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“…A simple procedure for the addition of mono and diarylacetylenes to indoles employs InBr 3 as an effective catalyst (Scheme ) . Activation of the alkyne is provided by the Lewis acid and the resulting 3‐akenyl indoles are predominantly obtained with E configuration.…”

Section: Hydroindolation Of Alkynes and Allenesmentioning

confidence: 99%

“…As imple procedure for the addition of mono and diarylacetylenes to indoles employs InBr 3 as an effectivec atalyst (Scheme 29). [82] Activation of the alkynei sp rovided by the Lewis acid and the resulting3 -akenyli ndoles are predominantly obtained with E configuration. The presence of substituents at C-2 favors the preferential formation of the Z stereoisomer as ar esult of at hermodynamic equilibration promoted by the Lewis acid.…”

Section: C-3 Hydroindolationsmentioning

confidence: 99%

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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“…For the synthesis and potential uses of indole derivatives, see: Bhuvaneswari et al (2007); Ghosh & Maiti (2007); Sakai et al (2008); Kakiuchi & Kochi (2008). For the general synthetic procedure and structure analysis of a derivative of the title compound, see: Bhaskar et al (2010). For standard bond lengths, see Allen et al (1987).…”

Section: Related Literaturementioning

confidence: 99%