First heterogeneously palladium-catalysed fully selective C3-arylation of free NH-indoles

Cusati, Giuseppe; Djakovitch, Laurent

doi:10.1016/j.tetlet.2008.02.130

Cited by 92 publications

(37 citation statements)

References 25 publications

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“…[133] Furthermore, Bellina et al showed that the palladiumcatalyzed direct arylation of indoles can be achieved at the C3-position by using either PCy 3 or Bn(nBu) 3 NCl as additives (Scheme 65). [134] The elegantly developed procedure relying on the use of the latter, as well as a heterogeneous catalytic system ([Pd(NH 3 ) 4 ] 2+ /NaY) employed by Djakovitch et al, [135,136] displayed a remarkably broad scope, which included efficient CÀH bond functionalizations of sterically more demanding 2-substituted indoles.…”

Section: Methodsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

2009

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The area of transition-metal-catalyzed direct arylation through cleavage of C-H bonds has undergone rapid development in recent years, and is becoming an increasingly viable alternative to traditional cross-coupling reactions with organometallic reagents. In particular, palladium and ruthenium catalysts have been described that enable the direct arylation of (hetero)arenes with challenging coupling partners--including electrophilic aryl chlorides and tosylates as well as simple arenes in cross-dehydrogenative arylations. Furthermore, less expensive copper, iron, and nickel complexes were recently shown to be effective for economically attractive direct arylations.

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Section: Methodsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

2009

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“…50 An electrophilic substitution in the arylation of 2-methylindole or 2-phenylindole using bromobenzene as the arylating agent occurs through the coordination of an Ar-Pd-X complex to indole nucleus has also been suggested on a [Pd(NH 3 ) 4 ] 2+ /NaY solid catalyst. 9 Therefore, we also tentatively propose the oxidation addition of Pd 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 21 After establishing the reaction conditions, we explored the symmetric diaryliodonium salt 2b (Table 3). Bis(4-methylphenyl)iodoniumtriflate was successfully employed to yield product 3b at a 94% yield.…”

Section: C-2 Arylation Of N-methylindoles In Watermentioning

confidence: 99%

An Efficient Reusable Mesoporous Solid-Based Pd Catalyst for Selective C2 Arylation of Indoles in Water

Duan

Zhang

et al. 2016

ACS Catal.

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The completely C2-selective arylation of N-methylindole was achieved by using a reusable solid Pd catalyst and water as a solvent without any other ligands or additives or exclusion of air. The catalysts possess well-dispersed Pd nanoparticles (~ 1.5 nm), N-containing functional groups (~ 11 wt%), and uniform mesopores (~ 5 nm). The turnover frequency (TOF) is calculated to be 82 h -1 .Arylations of both N-H indoles and N-protected indoles with diaryliodonium salts were achieved to give the desired products in high to excellent isolated yields in water.Mercapto-functionalized silica as a selective trapping agent, together with hot infiltration, confirms the undetected leaching of Pd. The catalyst samples can be reused at least 8 times without any additional activation treatment. The catalytic performance of the Pd catalyst is also compared with the performance of other mesoporous Pd catalysts on silica, carbon, and resins. The catalytic activity and stability of the present catalyst may be related to the well-dispersed Pd nanoparticles, the electron-rich environment stabilized by the N-containing functional groups, and the large, uniform mesopores.

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“…[133] Des weiteren zeigten Bellina et al, dass palladiumkatalysierte direkte Arylierungen an der C3-Position von Indolen bei Zusatz von PCy 3 oder Bn(nBu) 3 NCl möglich sind (Schema 65). [134] Das letztere der beiden Verfahren sowie eine [135,136] zeigte ein bemerkenswerte Anwendungsbreite, einschließlich der effizienten Funktionalisierung von C-H-Bindungen sterisch anspruchsvoller 2-substituierter Indole.…”

Section: Angewandte Chemieunclassified

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

2009

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Das Gebiet der übergangsmetallkatalysierten direkten Arylierung unter C‐H‐Bindungsbruch hat in den letzten Jahren eine rasante Entwicklung erfahren, was dazu führte, dass sich solche Methoden immer mehr als Alternativen zu den herkömmlichen Kreuzkupplungen mit metallorganischen Reagentien etabliert haben. Insbesondere wurden zahlreiche Palladium‐ und Rutheniumkatalysatoren beschrieben, welche die direkte Arylierung von (Hetero)arenen mit anspruchsvollen Reaktionspartnern ermöglichen; hierzu gehören elektrophile Arylchloride und ‐tosylate oder auch einfache Arene in gekreuzten dehydrierenden Arylierungen.

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First heterogeneously palladium-catalysed fully selective C3-arylation of free NH-indoles

Cited by 92 publications

References 25 publications

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

An Efficient Reusable Mesoporous Solid-Based Pd Catalyst for Selective C2 Arylation of Indoles in Water

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

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