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 7 publications

(1 citation statement)

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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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Regioselective Synthesis of Pyrrole‐Based Poly(arylenevinylene)s via Mn‐Catalyzed Hydroarylation Polyaddition

Tsukahara,

Iwamori,

Kuwabara

et al. 2024

Macromol. Rapid Commun.

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Mn‐catalyzed hydroarylation polyaddition of 1‐(2‐pyrimidinyl)pyrrole (1a) with aromatic diynes is investigated. The use of commercially available MnBr(CO)5 as a precatalyst under the optimized reaction conditions resulted in a site‐ and regioselective hydroarylation polyaddition, affording the corresponding poly(arylenevinylene)s (PAVs) with excellent vinylene selectivity. The reaction protocol eliminates the production of stoichiometric amounts of byproducts from the monomers. The nonstoichiometric polyaddition of an excess amount of 1a with aromatic diynes is also demonstrated. The 2‐pyrimidinyl substituent promoted the intramolecular transfer of the Mn catalyst walking through the 1a moiety.

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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 7 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

Regioselective Synthesis of Pyrrole‐Based Poly(arylenevinylene)s via Mn‐Catalyzed Hydroarylation Polyaddition

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