A Direct Palladium‐Catalyzed Route for the Synthesis of Benzo[<i>a</i>]carbazoles through Sequential C–C Bond Formation and C–H Bond Functionalization

Kianmehr, Ebrahim; Ghanbari, Mohammad

doi:10.1002/ejoc.201101401

Cited by 29 publications

(6 citation statements)

References 47 publications

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“…Due to their importance, a number of reliable methods for the preparation benzo[ a ]carbazole derivatives have been developed . Among them, a popular approach is to use diazo compounds as metal carbene precursors to form the required C−C bond(s) in constructing the benzo[ a ]carbazole scaffold ,,.…”

Section: Figurementioning

confidence: 99%

Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1‐a]‐Isoquinolines via Rh(III)‐Catalyzed C−H Functionalizations of 2‐Arylindoles with Sulfoxonium Ylides

et al. 2018

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A highly chem-and regioselective synthesis of diversely substituted benzo[a]carbazoles and indolo[2,1-a]-isoquinolines through Rh(III)catalyzed cascade reactions of 2-arylindoles with sulfoxonium ylides is presented. To be specific, treatment of 2-arylindoles, 2-arylindole-3-carbaldehydes, 2-arylindole-3-carbonitriles or 2-aryl-3-methylindoles with sulfoxonium ylides under the catalysis of Rh(III) led to the selective formation of 6aryl/alkyl benzo[a]carbazoles, 5-acylbenzo[a]carbazoles, 6-amino-5-acylbenzo[a]carbazoles or 12methylindolo[2,1-a]isoquinolines, respectively. Mechanistically, the formation of the title compounds involves a cascade process including metalation of the inert C(sp 2 )ÀH bond, migratory insertion of ylide into the carbon-metal bond via an in situ carbenoid formation, protodemetalation, and condensation. To our knowledge, this is the first example in which b-carbonyl sulfoxonium ylides were used as stable carbene precursors and bifunctional C2 synthons to afford benzo[a]carbazoles and indolo[2,1-a]isoquinolines.

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Section: Figurementioning

confidence: 99%

Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1‐a]‐Isoquinolines via Rh(III)‐Catalyzed C−H Functionalizations of 2‐Arylindoles with Sulfoxonium Ylides

et al. 2018

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“…The π-π interactions in prepared compound 8a synthetic method to benzo[a]carbazoles, we designed a direct palladium-catalyzed route for the synthesis of novel benzo[a]carbazoles through sequential C-C bond formation and C-H bond functionalization in one-pot by using readily available starting materials [47]. We now report full details of our study on the synthesis of benzo[a]carbazoles based on a preliminary communication.…”

Section: Figmentioning

confidence: 97%

Direct synthesis of benzo[a]carbazoles by palladium-catalyzed domino reactions: synthesis and photophysical properties of diverse benzo[a]carbazoles

et al. 2015

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“…[227] Recently, a variety of benzo[a]carbazole derivatives 359 was synthesized in good yields by Kanmehr and Ghanbari via a one-pot reaction sequence involving a base-catalyzed condensation reaction of N-unsubstituted and N-substituted 3-indolylacetonitriles 358 and ortho-bromobenzaldehydes followed by a Pd-catalyzed intramolecular arylation reaction under ligandless conditions (Scheme 181). [228] In 2011, hippadine (362), a 7H-pyrroloA C H T U N G T R E N N U N G [3,2,1-de]-phenanthridine alkaloid isolated from the bulbs of Brunsvigia josephinae,…”

Section: Ascwiley-vchdementioning

confidence: 99%

Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom

et al. 2014

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In recent years, transition metal-catalyzed direct (hetero)arylation reactions of heteroarenes with (hetero)aryl halides and pseudohalides have received significant attention as eco-friendly and economic alternatives to classical methods for the construction of heteroaryl-(hetero)aryl C À C bonds by transition metal-catalyzed cross-couplings involving the use of stoichiometric amounts of organometallic reagents. This critical review with 430 references covers the results obtained in the period January 2009 to February 2013 in the area of the transition metal-catalyzed direct inter-and intramolecular (hetero)arylation reactions of heteroarenes containing one heteroatom. Particular attention has been given to illustrate chemo-and site selectivity aspects of these reactions as well applications of these C À C bond forming reactions in the synthesis of pharmaceutically relevant compounds, natural products and their analogues and precursors. The most recent advancements into the mechanism(s) of these reactions have also been briefly reported.

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A Direct Palladium‐Catalyzed Route for the Synthesis of Benzo[a]carbazoles through Sequential C–C Bond Formation and C–H Bond Functionalization

Cited by 29 publications

References 47 publications

Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1‐a]‐Isoquinolines via Rh(III)‐Catalyzed C−H Functionalizations of 2‐Arylindoles with Sulfoxonium Ylides

Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1‐a]‐Isoquinolines via Rh(III)‐Catalyzed C−H Functionalizations of 2‐Arylindoles with Sulfoxonium Ylides

Direct synthesis of benzo[a]carbazoles by palladium-catalyzed domino reactions: synthesis and photophysical properties of diverse benzo[a]carbazoles

Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom

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