Palladium‐Catalyzed Oxidative Cyclization of <i>N</i>‐Aryl Enamines: From Anilines to Indoles

Würtz, Sebastian; Rakshit, Souvik; Neumann, Julia J.; Dröge, Thomas; Glorius, Frank

doi:10.1002/anie.200802482

Cited by 446 publications

(145 citation statements)

References 82 publications

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“…Thus, a variety of aryl ketones were efficiently functionalized in pinacolone (51) as the solvent with boronates bearing either electron-donating or electron-withdrawing substituents (Scheme 18). [28,29] Subsequently, this procedure was applied by Sames and co-workers to the catalytic functionalization of challenging C(sp 3 )ÀH bonds in saturated N heterocycles.…”

Section: Ruthenium-catalyzed Direct Arylationsmentioning

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: Ruthenium-catalyzed Direct Arylationsmentioning

confidence: 99%

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

2009

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“…Glorius and co-workers have recently described the one-pot synthesis of indoles from aniline using InBr 3 and PdA C H T U N G T R E N N U N G (OAc) 2 . [52] Fagnou and co-workers have reported the Rh-catalyzed intermolecular cyclization between alkynes and N-acetyl anilines. [53] Both of these methods represent significant advances for C À H activation, however, both of these methods suffer from the fact that they require directing groups for the coupling to proceed.…”

Section: Other Metalsmentioning

confidence: 99%

Beyond Traditional Cross Couplings: The Scope of the Cross Dehydrogenative Coupling Reaction

Scheuermann

2010

Chemistry An Asian Journal

642

104

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Dedicated to the 150th anniversary of Japan-UK diplomatic relations FOCUS REVIEWSAbstract: The development of new and environmentally compatible methods for the synthesis of CÀC and CÀhet-eroatom bonds is of great significance to researchers. The cross dehydrogenative coupling (CDC) is emerging as an important tool for chemists with a variety of, often inexpensive, metal catalysts able to perform these reactions both regio-and enantioselectively. Perhaps more importantly CDC methodology has been shown to be extremely environmentally friendly and facile being able to be carried out in aqueous environments under an atmosphere of air. This Focus Review intends to give an overview of the most contemporary developments in this exciting and emerging area of cross-coupling chemistry.

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“…60 The one-pot version of the reaction starting from commercially available anilines was also demonstrated. For meta-substituted anilines, the less hindered position was alkylated with excellent selectivities.…”

Section: Scheme 43mentioning

confidence: 99%

Construction of indole nucleus through C-H functionalization reactions

Song¹,

Reeves²,

Fandrick³

et al. 2010

Arkivoc

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This review article summarizes C-H functionalization-based synthesis of indoles and related structures (e.g. carbazoles and indolines) with an emphasis on literature after 2000. The discussion is organized into four broadly defined sections: a) via nitrene or carbene insertion into a C-H bond; b) via direct coupling of two sp 2 carbon centers; c) via transition-metal catalyzed C-H amination and d) other strategies.

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Palladium‐Catalyzed Oxidative Cyclization of N‐Aryl Enamines: From Anilines to Indoles

Cited by 446 publications

References 82 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

Beyond Traditional Cross Couplings: The Scope of the Cross Dehydrogenative Coupling Reaction

Construction of indole nucleus through C-H functionalization reactions

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