Liganden‐ und lösungsmittelkontrollierte regio‐ und chemodivergente Carbonylierungen

Peng, Jin‐Bao; Wu, Xiao‐Feng

doi:10.1002/ange.201709807

Angewandte Chemie

2018

DOI: 10.1002/ange.201709807

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Liganden‐ und lösungsmittelkontrollierte regio‐ und chemodivergente Carbonylierungen

Jin‐Bao Peng

Xiao‐Feng Wu

Abstract: Die Entwicklung hochselektiver Vorschriften ist eines der Kernziele der organischen Chemie. Unter den bekannten organischen Transformationen sind Carbonylierungen eine ideale Wahl für die Herstellung von Verbindungen mit Carbonylgruppen. In diesem Aufsatz werden die jüngsten Erfolge bei der Kontrolle der Selektivität von Carbonylierungsreaktionen zusammengefasst. Der Einfluss der Liganden, Lösungsmittel und Basen auf die Selektivität wird erläutert.

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Cited by 21 publications

References 100 publications

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Palladium‐Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

Peng

Chen

et al. 2018

Adv Synth Catal

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Alkyl aryl ketones are important structures with applications in many areas of chemistry. Hence, efficient procedures for their production are particularly attractive. In this communication, a general and efficient carbonylative cross-coupling of aryl iodides and unactivated alkyl bromides is presented. By using a simple palladium catalyst, a series of alkyl aryl ketones were synthesized in moderate to excellent yields from readily available alkyl and aryl halides in an In-Ex tube with formic acid as the CO source. In this study both primary and secondary alkyl bromides/iodides were suitable coupling partners. Additionally, this method can also be employed for the late-stage functionalization of complex natural products and polyfunctionalized molecules.

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Palladium‐Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

Peng

Chen

et al. 2018

Adv Synth Catal

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Catalytic Chemodivergent Annulations ofo‐Aminotrifluoroacetophenone and Allenyl Imide through β’‐C−H Functionalization or β/γ‐Bisfunctionalization

et al. 2022

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Lewis base and Brønsted base controlled chemodivergent annulations of α-methyl substituted allenyl imide and o-aminotrifluoroacetophenones are realized to afford highly valuable furo[3,2-b]indol-2-ones and dihydroquinolines bearing a CF 3 -substituted quaternary stereogenic center. The possible reaction mechanisms are proposed through deuterium labelling experiments. This work demonstrates the unprecedented dual reactivities of α-methyl substituted allenyl imide with electrophilicÀ nucleophilic compounds in annulation reactions, and features chemodivergence in transforming allenyl imide through β'-CÀ H functionalization via phosphine catalysis and β/γ-bisfunctionalization via Brønsted base catalysis.

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Recent Developments in the C(sp³)−H Functionalization of 2‐Oxindoles through Radical Reactions

Chen

2018

Asian J Org Chem

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Abstract3‐Substituted 2‐oxindoles are prevalent in a variety of natural products and bioactive compounds. As such, the synthesis of these molecules is highly desirable. This Focus Review provides a critical overview of recent developments (in particular, reports since 2013) in the C(sp3)−H functionalization of 2‐oxindoles through radical reactions. The main achievements in this field are presented according to the bonds that are formed. Special attention is paid to the reaction mechanisms, and a personal outlook on future developments in this research area is provided.

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Liganden‐ und lösungsmittelkontrollierte regio‐ und chemodivergente Carbonylierungen

Cited by 21 publications

References 100 publications

Palladium‐Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

Palladium‐Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

Catalytic Chemodivergent Annulations ofo‐Aminotrifluoroacetophenone and Allenyl Imide through β’‐C−H Functionalization or β/γ‐Bisfunctionalization

Recent Developments in the C(sp³)−H Functionalization of 2‐Oxindoles through Radical Reactions

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Liganden‐ und lösungsmittelkontrollierte regio‐ und chemodivergente Carbonylierungen

Cited by 21 publications

References 100 publications

Palladium‐Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

Palladium‐Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

Catalytic Chemodivergent Annulations ofo‐Aminotrifluoroacetophenone and Allenyl Imide through β’‐C−H Functionalization or β/γ‐Bisfunctionalization

Recent Developments in the C(sp3)−H Functionalization of 2‐Oxindoles through Radical Reactions

Contact Info

Product

Resources

About

Recent Developments in the C(sp³)−H Functionalization of 2‐Oxindoles through Radical Reactions