Nickel-Catalyzed Addition of C–C Bonds of Amides to Strained Alkenes: The 1,2-Carboaminocarbonylation Reaction

Ito, Yuri; Nakatani, Syun; Shiraki, Ryota; Kodama, Takuya; Tobisu, Mamoru

doi:10.1021/jacs.1c09265

Cited by 25 publications

(15 citation statements)

References 30 publications

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“…In 2022, the Tobisu group explored a two-component carboacylation of norbornene derivatives. Exploiting a Ni/NHC system, the authors were able to develop an entirely atom-economic carboacylation process utilizing N- indoyl arylamides [ 38 ].…”

Section: Reviewmentioning

confidence: 99%

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Pounder¹,

Neufeld²,

Myler³

et al. 2023

Beilstein J. Org. Chem.

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This review presents a comprehensive overview of transition-metal-catalyzed domino reactions of strained bicyclic alkenes, including both homo- and heterobicyclic alkenes. These compounds are important synthons in organic synthesis, providing an important platform for the construction of biologically/medicinally significant compounds which bear multiple stereocenters. The review has been divided according to the metal used in the reaction. An overview of the substrate scope, reaction conditions, and their potential applications in organic synthesis is discussed. A comprehensive outlook on the reactivity paradigms of homo- and heterobicyclic alkenes is discussed and should shed light on future directions for further development in this field.

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Section: Reviewmentioning

confidence: 99%

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Pounder¹,

Neufeld²,

Myler³

et al. 2023

Beilstein J. Org. Chem.

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“…Transition metal-catalyzed dicarbofunctionalization of alkenes represents a powerful tool for the rapid construction of complex molecular architectures from simple and readily available alkenes. Such transformations involving intramolecular carbometalation of alkenes followed by intermolecular nucleophilic or electrophilic trapping of the resulting σ-alkyl-metal intermediate have been extensively explored . Thanks to its unique characteristics, nickel has been used in a range of ligand-controlled divergent transformations and is therefore considered to be a potential catalyst to realize our hypothesis.…”

Section: Introductionmentioning

confidence: 99%

Switchable 1,2-Rearrangement Enables Expedient Synthesis of Structurally Diverse Fluorine-Containing Scaffolds

et al. 2022

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Skeletal rearrangement that changes the connectivity of the molecule via cleavage and reorganization of carbon–carbon bonds is a fundamental and powerful strategy in complex molecular assembly. Because of the lack of effective methods to control the migratory tendency of different groups, achieving switchable selectivity in skeletal rearrangement has been a long-standing quest. Metal-based dyotropic rearrangement provides a unique opportunity to address this challenge. However, switchable dyotropic rearrangement remains unexplored. Herein, we show that such a problem could be solved by modifying the ligands on the metal catalyst and changing the oxidation states of the metal to control the migratory aptitude of different groups, thereby providing a ligand-controlled, switchable skeletal rearrangement strategy. Experimental and density functional theory calculation studies prove this rational design. The rearrangement occurs only when the nickel(II) intermediate is reduced to a more nucleophilic nickel(I) species, and the sterically hindered iPrPDI ligand facilitates 1,2-aryl/Ni dyotropic rearrangement, while the terpyridine ligand promotes 1,2-acyl/Ni dyotropic rearrangement. This method allows site-selective activation and reorganization of C–C bonds and has been applied for the divergent synthesis of four medicinally relevant fluorine-containing scaffolds from the same starting material.

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“…Scheme 59 NHC/Ni-catalysed regioselective diarylation of aliphatic 1,3dienes 144. Scheme 60 NHC/Ni-catalysed 1,2-carboaminocarbonylation of strained alkenes via C-C bond activation of amides 146. …”

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confidence: 99%

N-Heterocyclic carbenes as privileged ligands for nickel-catalysed alkene functionalisation

et al. 2023

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Nickel-Catalyzed Addition of C–C Bonds of Amides to Strained Alkenes: The 1,2-Carboaminocarbonylation Reaction

Abstract: C(aryl)−C(O) bonds of aryl amides can be activated and added across alkenes with the aid of a nickel catalyst. This 1,2-carboaminocarbonylation reaction enables the dicarbofunctionalization of alkenes with an atom economy of 100%.

Cited by 25 publications

References 30 publications

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

Switchable 1,2-Rearrangement Enables Expedient Synthesis of Structurally Diverse Fluorine-Containing Scaffolds

N-Heterocyclic carbenes as privileged ligands for nickel-catalysed alkene functionalisation

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