An Approach to 3-(Indol-2-yl)succinimide Derivatives by Manganese-Catalyzed C–H Activation

Liu, Shuang‐Liang; Yang, Li; Guo, Jun-Ru; Yang, Guang‐Chao; Li, Xuehong; Gong, Jun‐Fang; Song, Mao‐Ping

doi:10.1021/acs.orglett.7b01795

Cited by 111 publications

(43 citation statements)

References 75 publications

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“…Although the C2-alkylation of N-(2-pyri(mi)dyl)indoles with alkenes can be catalyzed by ar ange of metals including ruthenium, [162] cobalt, [168c, 192] manganese, [193] and rhodium, [194] Ackermannss electivity-switchable,c obalt-catalyzed alkylation [192b] is probably the most versatile method reported to date (Scheme 40). Te rminal unactived alkenes could indeed be used for the C2-alkylation of N-(2-pyridyl)indoles with catalytic amounts of Cp*Co(CO)I 2 and AgSbF 6 ,w ithout or with 1-adamantylcarboxylic acid to provide linear or branched products,respectively.Detailed mechanistic studies revealed ac hange in the mechanism from al inear-selective ligand-to-ligand hydrogen transfer to ab ranched-selective carboxylate-assisted internal electrophilic-type substitution in the presence of the carboxylate additive.A ne specially efficient and appealing enantioselective version based on the use of ac hiral carboxylic acid was moreover reported recently.…”

Section: Alkylation With Alkenesmentioning

confidence: 99%

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

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The alkylation of arenes is one of the most fundamental transformations in chemical synthesis leading to privileged scaffolds in many areas of science. Classical methods for the introduction of alkyl groups to arenes are mostly based on the Friedel-Crafts reaction, radical additions, metallation or pre-functionalization of the arene: these methods however suffer from limitations in scope, efficiency and selectivity. Moreover, they are based on the innate reactivity of the starting arene, favoring the alkylation at a certain position and rendering the introduction of alkyl chains at other positions much more challenging. This can be addressed by the use of a directing group facilitating, in the presence of a metal catalyst, the regioselective alkylation of a C-H bond. These directed alkylations of C-H bonds in arenes are overviewed, in a comprehensive manner, in this review article.

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Section: Alkylation With Alkenesmentioning

confidence: 99%

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

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“…This type of addition reaction has been successfully extended with manganese catalyst by Song and his co‐workers. When N ‐pyridylindole ( 12 a ) was treated with N ‐phenylmaleimide ( 13 a ) in the presence of Mn 2 (CO) 10 (10 mol%) at 120 °C in EtOAc, a C‐2 alkylated indole derivative 14 a was observed in 90% yield (Scheme ) . Interestingly, the neutral manganese complex effectively catalyzed the reaction under air atmosphere.…”

Section: Ortho Alkylation Of Aromatics With Maleimidesmentioning

confidence: 99%

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

2019

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Maleimide and succinimide core moieties are present in various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important organic molecules including pyrrolidines and γ-lactams. A transition-metal-catalyzed chelationassisted functionalization of inert CÀ H bond of organic molecules with electrophiles or nucleophiles is one of the efficient methods to construct chemical bonds in a highly atom-and step-economical manner. The present review describes the recent advances in the reaction involving maleimides with organic molecules by a chelation-assisted inert CÀ H bond activation methodology. The reaction involving maleimides with organic molecules having directing groups, such as ketone, acyl, pyridyl, pyrimidyl, oxime, amide, imidate, chromone, azo, N-sulfonyl ketimine, carboxylic acids, and aldimines, were described. The scope, limitation and mechanistic investigation of the alkylation, annulation and alkenylation reactions were discussed elaborately. This review article includes the entire report on the chemical bondforming reaction of maleimides with organic molecules by the CÀ H bond activation strategy until the end of 2018.

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“…Die C2-Alkylierung von N-(2-Pyri(mi)dyl)indolen mit Alkenen kann von diversen Metallen katalysiert werden, einschließlich Ruthenium, [162] Cobalt, [168c, 192] Mangan [193] und Schema 39. Palladium-und rhodiumkatalysierte ortho-Alkylierung von 2-(N-Heteroaryl)arenen mit Alkylborreagentien.…”

Section: Alkylierung Mit Alkenenunclassified

Jenseits von Friedel und Crafts: dirigierte Alkylierung von C‐H‐Bindungen in Arenen

Evano

Theunissen

2019

Angewandte Chemie

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Die Alkylierung von Arenen ist eine der grundlegendsten Transformationen in der chemischen Synthese und führt in vielen wissenschaftlichen Bereichen zu privilegierten Molekülgerüsten. Klassische Methoden für die Einführung von Alkylgruppen in Arene beruhen zumeist auf der Friedel‐Crafts‐Reaktion, Radikaladditionen, Metallierungen oder Präfunktionalisierungen von Arenen; die Anwendungsbreite, Effizienz und Selektivität dieser Methoden sind jedoch begrenzt. Außerdem bauen sie auf der inhärenten Reaktivität des Ausgangsarens auf, die die Alkylierung in einer bestimmten Position bevorzugt und die Einführung von Alkylketten an anderen Stellen wesentlich schwieriger macht. Dieses Problem kann durch die Verwendung einer dirigierenden Gruppe angegangen werden, die in Gegenwart eines Metallkatalysators die regioselektive Alkylierung einer C‐H‐Bindung vereinfacht. Diese dirigierten Alkylierungen von C‐H‐Bindungen in Arenen werden im vorliegenden Aufsatz zusammengefasst.

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An Approach to 3-(Indol-2-yl)succinimide Derivatives by Manganese-Catalyzed C–H Activation

Cited by 111 publications

References 75 publications

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

Jenseits von Friedel und Crafts: dirigierte Alkylierung von C‐H‐Bindungen in Arenen

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