Manganese-catalyzed hydroarylation of multiple bonds

Maayuri, Rajaram; Gandeepan, Parthasarathy

doi:10.1039/d2ob01674e

Org. Biomol. Chem.

2023

DOI: 10.1039/d2ob01674e

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Manganese-catalyzed hydroarylation of multiple bonds

Rajaram Maayuri

Parthasarathy Gandeepan

Abstract: The developments in the field of manganese-catalyzed hydroarylation of multiple bonds via C–H activation with a range of applications are highlighted in this review article.

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Cited by 10 publications

(1 citation statement)

References 174 publications

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“…Over the past two decades, transition metal-catalysed C–H bond activation 6 has emerged as a valuable approach for constructing complex molecular scaffolds. Rh( iii ) complexes, 7 in particular, have been instrumental in catalysing annulation reactions.…”

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confidence: 99%

Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to synthesize unsubstituted 1-aminoindole derivatives

Chen,

Lu,

et al. 2024

RSC Adv.

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confidence: 99%

Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to synthesize unsubstituted 1-aminoindole derivatives

Chen,

Lu,

et al. 2024

RSC Adv.

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Rhodium(III)‐Catalyzed C−H/N−H Activation for Direct Synthesis of Pyrimidoindolones under Mild Conditions

Kumar,

Maayuri,

Medhi

et al. 2023

Chemistry An Asian Journal

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Pyrimidoindolones are an important structural motif found in many natural products and are essential to the pharmaceutical and agrochemical industry. Direct synthesis of 3,4‐unsubstituted pyrimidoindolones is not easily accessible. Here we report a rhodium(III)‐catalyzed C‒H/N‒H activation and annulation approach for obtaining pyrimidoindolones from N‐carbamoylindoles and vinylene carbonate. The reaction occurs at room temperature and does not require any external oxidants. A diverse spectrum of indoles were demonstrated to be viable substrates capable of producing the desired pyrimidoindolones in high yields. In addition, the reaction's scope has been expanded to include pyrrole substrate. Furthermore, detailed mechanistic studies have been performed to delineate the working mode of the reaction.

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Synthesis of 3‐Methyleneisoindolin‐1‐ones via Rhodium(III)‐Catalyzed C−H/N−H Activation and Annulation of N‐Methoxybenzamides with Potassium Vinyltrifluoroborate

Kumar,

Gandeepan

2024

Chemistry An Asian Journal

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Isoindolinones are vital heterocyclic compounds in medicinal chemistry, notable for their diverse bioactivities. Significant attention has been devoted to their preparation; however, existing methods are unsuitable for constructing unsubstituted 3‐methyleneisoindolin‐1‐ones. Herein, we present a rhodium(III)‐catalyzed method for synthesizing unsubstituted 3‐methyleneisoindolin‐1‐ones via C‒H/N‒H activation and annulation of N‐methoxybenzamides with potassium (ethenyl)trifluoroborate. This approach offers mild reaction conditions, high regioselectivity, and efficient yields. Interestingly, sterically demanding or heterocyclic N‐methoxyaromaticamides resulted in the formation of 2‐vinyl(hetero)aromatic amides instead of 3‐methyleneisoindolin‐1‐ones. Mechanistic insights suggest a rhodacycle intermediate pathway, highlighting the method's potential for developing new bioactive isoindolinone derivatives.

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Manganese-catalyzed hydroarylation of multiple bonds

Abstract: The developments in the field of manganese-catalyzed hydroarylation of multiple bonds via C–H activation with a range of applications are highlighted in this review article.

Cited by 10 publications

References 174 publications

Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to synthesize unsubstituted 1-aminoindole derivatives

Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to synthesize unsubstituted 1-aminoindole derivatives

Rhodium(III)‐Catalyzed C−H/N−H Activation for Direct Synthesis of Pyrimidoindolones under Mild Conditions

Synthesis of 3‐Methyleneisoindolin‐1‐ones via Rhodium(III)‐Catalyzed C−H/N−H Activation and Annulation of N‐Methoxybenzamides with Potassium Vinyltrifluoroborate

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