<i>N</i>-H Carbazole Synthesis from 2-Chloroanilines via Consecutive Amination and C−H Activation

Bedford, Robin B.; Betham, Michael

doi:10.1021/jo061749g

Cited by 174 publications

(71 citation statements)

References 28 publications

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“…This approach was more recently applied to the synthesis of free NH and fluorinated carbazoles. [163,164] We developed a direct arylation-based domino reaction, which enabled the efficient synthesis of various N heterocycles, such as indoles and carbazoles, and notably, proved applicable to substrates bearing solely chlorides as leaving groups. [165] This modular one-pot transformation of 1,2-dichlorides proceeded regioselectively to deliver both Nsubstituted and free NH carbazoles (Scheme 81).…”

Section: Aryl Chloridesmentioning

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: Aryl Chloridesmentioning

confidence: 99%

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

2009

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“…Der Ansatz wurde neuerlich zur Synthese von freien NH-und fluorierten Carbazolen verwendet. [163,164] Wir entwickelten eine auf einer direkten Arylierung basierende Dominoreaktion, welche die effiziente Synthese verschiedener N-Heterocyclen wie Indole und Carbazole ermöglichte und bemerkenswerterweise auf Substrate mit Chloriden als einzigen Abgangsgruppen übertragen werden konnte. [165] Diese modulare Eintopfreaktion von 1,2-Dichloriden führte regioselektiv zu sowohl N-substituierten als auch freien NH-Carbazolen (Schema 81).…”

Section: Arylchlorideunclassified

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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“…[23,24] The Ackermann group showed one example on N-9-substituted 9H-a-carboline synthesis, namely 9-phenyl-3-trifluoromethyl-9H-pyridoA C H T U N G T R E N N U N G [2,3-b]indole. [24] Similarly, our research group recently published reaction conditions for tandem Pd-catalyzed synthesis of substituted benzo-g-carbolines (11H-indoloA C H T U N G T R E N N U N G [3,2-c]quinolines).…”

Section: Entrymentioning

confidence: 99%

Synthesis of α‐Carbolines Starting from 2,3‐Dichloropyridines and Substituted Anilines

et al. 2008

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9H-a-Carbolines have been prepared via consecutive intermolecular Buchwald-Hartwig reaction and Pd-catalyzed intramolecular direct arylation from commercially available 2,3-dichloropyridines and substituted anilines. The combination of a high reaction temperature (180 8C) and the use of DBU were found to be crucial for the intramolecular direct arylation reactions of the 3-chloro-N-phenylpyridin-2-amines as no reaction was observed at 120 8C and 180 8C using different inorganic and other organic bases. On the other hand, nitrogenmethylated pyridine analogues of these substrates {N-[3-chloro-1-methylpyridin-2(1H)-ylidene]anilines} do undergo ring closure at 120 8C, with K 3 PO 4 as base, affording the respective 1-methyl-1H-a-carbolines in good yields.

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N-H Carbazole Synthesis from 2-Chloroanilines via Consecutive Amination and C−H Activation

Cited by 174 publications

References 28 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

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

Synthesis of α‐Carbolines Starting from 2,3‐Dichloropyridines and Substituted Anilines

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