Rh‐Catalyzed Synthesis of Nitrogen‐Containing Heterocycles

Muralirajan, Krishnamoorthy; Cheng, Chien‐Hong

doi:10.1002/9783527691920.ch5

Transition Metal‐Catalyzed Heterocycle Synthesis via CH Activation 2016

DOI: 10.1002/9783527691920.ch5

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Rh‐Catalyzed Synthesis of Nitrogen‐Containing Heterocycles

Krishnamoorthy Muralirajan

Chien‐Hong Cheng

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2024

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Cited by 3 publications

References 143 publications

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Tunable Rh(III)-Catalyzed C(sp²)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups

Wang,

Zeng

et al. 2024

Org. Lett.

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A tunable Rh(III)-catalyzed C(sp 2 )−H bond functionalization of aryl imidates with cyclic 1,3-diones was developed. With suitable and straightforward reaction condition adjustments, the C−H bond functionalization of diverse aryl imidates with cyclic 1,3-diones occurred smoothly and precisely at room temperature. Accompanied by different directing group transformations, a series of corresponding aryl nitriles, hydrophenanthridin-1(2H)-ones, spiro isoindoles, or hydrophenanthridine-1,6(2H,5H)-diones were synthesized in good yields to provide a rational directing group utilization strategy for the Rh(III)-catalyzed C(sp 2 )−H bond activation. Control experiments and primary mechanistic studies revealed that solvent effects and functional group electronic effects might influence the reaction's selectivity.

show abstract

Tunable Rh(III)-Catalyzed C(sp²)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups

Wang,

Zeng

et al. 2024

Org. Lett.

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Recent Advances in the Trifluoromethylation Reactions of Isonitriles To Construct CF3-Substituted N-Heterocycles

Kiss¹,

Aradi²

2023

Synthesis

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Due to the increasing need of fluorine-containing drugs, the synthesis of organofluorine scaffolds has become a highly researched area of synthetic organic chemistry. The introduction of the trifluoromethyl group onto the structure of an organic molecule has considerable potential and several advantages concerning the characteristics of the fluorinated pharmaceuticals. The incorporation of a CF3 group onto multiple bonds containing a nitrogen heteroatom is a relatively new field and currently it is an expanding area of synthetic chemistry; however it has not been reviewed so far. This short review summarizes recent developments in trifluoromethylation reactions of isonitriles.

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Rhodium(III)-Catalyzed C–H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds

Barber

Kong²,

Li³

et al. 2021

Synlett

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We describe a simple and robust procedure for the Rh(III)-catalyzed [4+2] cycloaddition of feedstock gases enabled through C–H activation. A diverse set of 3,4-dihydroisoquinolones and 3-methylisoquinolones have been prepared in good to excellent yields. The effects of using ethylene and propyne as coupling partners on C–H site selectivity have also been explored with a representative set of substrates and are discussed herein.

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Rh‐Catalyzed Synthesis of Nitrogen‐Containing Heterocycles

Cited by 3 publications

References 143 publications

Tunable Rh(III)-Catalyzed C(sp²)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups

Tunable Rh(III)-Catalyzed C(sp²)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups

Recent Advances in the Trifluoromethylation Reactions of Isonitriles To Construct CF3-Substituted N-Heterocycles

Rhodium(III)-Catalyzed C–H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds

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Rh‐Catalyzed Synthesis of Nitrogen‐Containing Heterocycles

Cited by 3 publications

References 143 publications

Tunable Rh(III)-Catalyzed C(sp2)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups

Tunable Rh(III)-Catalyzed C(sp2)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups

Recent Advances in the Trifluoromethylation Reactions of Isonitriles To Construct CF3-Substituted N-Heterocycles

Rhodium(III)-Catalyzed C–H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds

Contact Info

Product

Resources

About

Tunable Rh(III)-Catalyzed C(sp²)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups

Tunable Rh(III)-Catalyzed C(sp²)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups