Oxidative 1,2-carboamination of alkenes with alkyl nitriles and amines toward γ-amino alkyl nitriles

Liu, Yan‐Yun; Yang, Xu‐Heng; Song, Ren‐Jie; Luo, Shenglian; Li, Jin‐Heng

doi:10.1038/ncomms14720

Cited by 148 publications

(30 citation statements)

References 85 publications

(222 reference statements)

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“…Renaud and co-workers developed a carboazidation of alkenes 1 employing electrophilic alkyl radicals generated from ethyl α-iodoacetate and phenylsulfonyl azide as the azide sources 49 , 50 . Three-component 1,2-azido alkylation of alkenes with nucleophilic alkyl radical is to the best of our knowledge unknown 51 – 53 . The α-methylstyrene ( 1a ) was chosen as a test substrate for the optimization of the 1,2-azido methylation process.…”

Section: Resultsmentioning

confidence: 99%

Copper-catalyzed methylative difunctionalization of alkenes

Bao

Yokoe

et al. 2018

Nat Commun

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Trifluoromethylative difunctionalization and hydrofunctionalization of unactivated alkenes have been developed into powerful synthetic methodologies. On the other hand, methylative difunctionalization of olefins remains an unexplored research field. We report in this paper the Cu-catalyzed alkoxy methylation, azido methylation of alkenes using dicumyl peroxide (DCP), and di-tert-butyl peroxide (DTBP) as methyl sources. Using functionalized alkenes bearing a tethered nucleophile (alcohol, carboxylic acid, and sulfonamide), methylative cycloetherification, lactonization, and cycloamination processes are subsequently developed for the construction of important heterocycles such as 2,2-disubstituted tetrahydrofurans, tetrahydropyrans, γ-lactones, and pyrrolidines with concurrent generation of a quaternary carbon center. The results of control experiments suggest that the 1,2-alkoxy methylation of alkenes goes through a radical-cation crossover mechanism, whereas the 1,2-azido methylation proceeds via a radical addition and Cu-mediated azide transfer process.

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Section: Resultsmentioning

confidence: 99%

Copper-catalyzed methylative difunctionalization of alkenes

Bao

Yokoe

et al. 2018

Nat Commun

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“…In 2017, Luo and Li described a three-component Ag-mediated Fe-catalyzed 1,2-carboamination of alkenes 82 using alkyl nitriles 76 and amines 105 for the synthesis of γ-amino alkyl nitriles 106 ( Scheme 21 ) [ 104 ]. The use of Ag 2 CO 3 as a SET oxidant was shown to be key for the success of the reaction, as typical organic oxidants, like peroxides, displayed low activity.…”

Section: Reviewmentioning

confidence: 99%

Iron-catalyzed domino coupling reactions of π-systems

Pounder¹,

Tam²

2021

Beilstein J. Org. Chem.

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The development of environmentally benign, inexpensive, and earth-abundant metal catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal, homogenous iron catalysis they bear the chance to enable coupling reactions that rival that of noble-metal-catalysis. This review provides an overview of iron-catalyzed domino coupling reactions of π-systems. The classifications and reactivity paradigms examined should assist readers and provide guidance for the design of novel domino reactions.

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“…[25][26][27][28] Consequently, the transition-metal-catalyzed or the radical-mediated 1,2-/2,1-carboamination of alkenes is particularly popular and provides efficient approaches to generate the versatile nitrogen-containing architectures (Scheme 1a). [29][30][31][32][33][34][35][36][37][38][39][40][41] For instance, Piou and Rovis 39 achieved a rhodium-catalyzed diastereoselective syn -carboamination of alkenes with enoxyphthalimide in 2015. In 2018, Stephenson and co-workers 40 disclosed a photocatalytic 1,2-aminoarylation of alkenes with arylsulfonylacetamides as the bifunctional reagents.…”

Section: Introductionmentioning

confidence: 99%

Site-Selective Palladium-Catalyzed 1,1-Arylamination of Terminal Alkenes

et al. 2022

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Many of the commonly used pharmaceuticals and biologically active natural products are nitrogencontaining compounds. Recently, the transitionmetal-catalyzed or the radical-mediated 1,2-carboamination of alkenes has been well explored to access amine scaffolds. However, synthetic strategies toward the 1,1-carboamination of alkenes are severely limited. Herein, we describe a method to achieve the 1,1arylamination using readily available building blocks enabled by palladium catalysis. This sequential three step-Heck arylation, metal migration, followed by aza-1,6-Micheal addition process exhibits excellent chemo-and regioselectivity. To showcase the potential as a method for diversity-oriented drug discovery, the modification of numerous structurally complex bioactive molecules was also successfully performed.

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Oxidative 1,2-carboamination of alkenes with alkyl nitriles and amines toward γ-amino alkyl nitriles

Cited by 148 publications

References 85 publications

Copper-catalyzed methylative difunctionalization of alkenes

Copper-catalyzed methylative difunctionalization of alkenes

Iron-catalyzed domino coupling reactions of π-systems

Site-Selective Palladium-Catalyzed 1,1-Arylamination of Terminal Alkenes

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