Indoles from Simple Anilines and Alkynes: Palladium‐Catalyzed CH Activation Using Dioxygen as the Oxidant

Shi, Zhuangzhi; Zhang, Chun; Li, Si; Pan, Delin; Ding, Shengtao; Cui, Yuxin; Jiao, Ning

doi:10.1002/anie.200901484

Cited by 389 publications

(102 citation statements)

References 103 publications

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“…Jiaos group [20] reported a PdA C H T U N G T R E N N U N G (OAc) 2 (10 mol%) catalyzed indole synthesis from simple anilines and alkynes using dioxygen as the oxidant (Figure 15). All para-, meta-, and ortho-substituted anilines bearing electron-withdrawing or -donating groups were smoothly transformed into the desired products in 38-99% yield.…”

Section: Construction Of Indoles (Intramolecular Cyclizations or Intementioning

confidence: 99%

“…Dibenzofurans were obtained in good yields; 2-anilinonaphthoquinone and N-benzoylindoles are also good substrates, giving rise to the corresponding cyclized products. Cyclizations occurred exclusively in cases where two regioisomers could be obtained, except for one example (19)(20)(21)(22). Three naturally occurring, electron-rich tricyclic carbazoles were synthesized with pivalic acid as the solvent with improved reactivity and yields (Scheme 4).…”

Section: Construction Of Carbazoles (Intramolecular Cya C H T U N G Tmentioning

confidence: 99%

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Construction of Heterocycle Scaffolds via Transition Metal‐ Catalyzed sp² CH Functionalization

Zhang¹

2009

Adv Synth Catal

156

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Recently, the C À H functionalization strategy for the construction of heterocycles has received substantial attention because of its economic, sustainable and environmentally benign features. Many kinds of heterocycles have been synthesized via transition metal-catalyzed sp 2 C À H functionalization. The new strategy for the construction of heterocycle scaffolds includes intramolecular cyclizations and intermolecular cyclizations, namely multicomponent reactions (MCRs) that achieve the formation of multiple bonds in one operation. This review introduces the synthesis of carbazoles, benzoxazoles, benzimid-A C H T U N G T R E N N U N G azoles, 2-substituted benzothiazoles, 3-aryl/alkylind-A C H T U N G T R E N N U N G azoles, indoles, oxindoles, indolines, benzolactams, phthalimides, dibenzofurans and bridgehead unsaturated bicyclic enamines by the new strategy. The orientation of the cyclizations depends mainly on steric factors in cases where two regioisomers can be obtained. The regioselectivity of cyclizations is high in most cases, the cyclizations are even exclusive to give one sole product without the regioisomer in some cases. The functional group tolerance is good in most cases, halogen atoms and even iodine atoms are tolerated by the new strategy in some cases, providing a handle for further functionalization. The described strategy is being rapidly developed. Versatile features of the strategy have emerged, this review tries to classify the reported methods and inspire further investigations.

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Section: Construction Of Indoles (Intramolecular Cyclizations or Intementioning

confidence: 99%

Section: Construction Of Carbazoles (Intramolecular Cya C H T U N G Tmentioning

confidence: 99%

Construction of Heterocycle Scaffolds via Transition Metal‐ Catalyzed sp² CH Functionalization

Zhang¹

2009

Adv Synth Catal

156

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“…59 The reaction does involve a formal C-H activation, but it was suggested to take place in the alkenylpalladium intermediate formed after addition of the amine to the alkyne. The C-H cleavage step has been proposed to involve an electrophilic aromatic palladation (Scheme 35).…”

Section: Annulations Involving a Migratory Insertion Step Before The mentioning

confidence: 99%

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

2016

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Abstract:The exponential increase in the number of catalytic transformations that involve a metal-promoted activation of hitherto considered inert C-H bonds is promoting a paradigmatic change in the field of synthetic chemistry. While most reactions involving C-H activations consist of simple functionalizations or additions, recent years have witnessed a boost on related transformations that can be formally considered as cycloaddition processes. These transformations are particularly appealing from a synthetic perspective because they allow the conversion of readily available substrates into highly valuable cyclic products in a rapid and sustainable manner. In many cases, these annulations involve the formation of metallacyclic intermediates that resemble those proposed for standard metalcatalyzed cycloadditions of unsaturated precursors.

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“…Recently, Jiao and co-workers have reported the use of a palladium catalyst of the synthesis of indoles from anilines and alkynes using molecular oxygen as the oxidant, Scheme 33. [54] The use of molecular oxygen represents a significant improvement on the use of other chemical oxidants, such as CuA C H T U N G T R E N N U N G (OAc) 2 , AgOAc, and PhIA C H T U N G T R E N N U N G (OAc) 2 , as it is considered a green and sustainable oxidant thus rendering this reaction industrially relevant.…”

Section: Other Metalsmentioning

confidence: 99%

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

Scheuermann

2010

Chemistry An Asian Journal

636

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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Indoles from Simple Anilines and Alkynes: Palladium‐Catalyzed CH Activation Using Dioxygen as the Oxidant

Cited by 389 publications

References 103 publications

Construction of Heterocycle Scaffolds via Transition Metal‐ Catalyzed sp² CH Functionalization

Construction of Heterocycle Scaffolds via Transition Metal‐ Catalyzed sp² CH Functionalization

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

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

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Indoles from Simple Anilines and Alkynes: Palladium‐Catalyzed CH Activation Using Dioxygen as the Oxidant

Cited by 389 publications

References 103 publications

Construction of Heterocycle Scaffolds via Transition Metal‐ Catalyzed sp2 CH Functionalization

Construction of Heterocycle Scaffolds via Transition Metal‐ Catalyzed sp2 CH Functionalization

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

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

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Product

Resources

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Construction of Heterocycle Scaffolds via Transition Metal‐ Catalyzed sp² CH Functionalization

Construction of Heterocycle Scaffolds via Transition Metal‐ Catalyzed sp² CH Functionalization