Cobalt-catalyzed cross-coupling of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium reagents

Cui, Yan-Ying; Na, Jin-He; Guo, Minzhe; Huang, Jie-Ying; Chu, Xiangcheng; Rao, Weidong; Shen, Zhi‐Liang

doi:10.1016/j.tetlet.2022.153662

Cited by 7 publications

(1 citation statement)

References 50 publications

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“…Recently, nitrogen-containing heterocyclic phosphonium salts , have received considerable attention. They were found to function as versatile electrophiles for heteroarylation, capable of undergoing a variety of organic transformations with the transfer of the heterocycle scaffold to provide an easy entry to nitrogen-containing heterocyclic compounds.…”

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confidence: 99%

Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne

Zhang

Wang

et al. 2022

Org. Lett.

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An efficient Sonogashira coupling of a heterocyclic phosphonium salt with a terminal alkyne via C–P bond cleavage was developed. The reactions proceeded smoothly in the presence of palladium catalyst, copper(I) iodide, and N,N-diisopropylethylamine (DIPEA) in N-methyl-2-pyrrolidone (NMP) at 100 °C for 12 h, producing the corresponding alkynyl-substituted pyridine, quinoline, pyrazine, and quinoxaline in moderate to good yields with wide substrate scope and broad functional group tolerance. In addition, gram-scale synthesis could also be achieved, and the reaction could be applied to the functionalization of alkyne-containing complex molecules derived from sugars and pharmaceutical and naturally occurring products (e.g., estrone, d-galactopyranose, menthol, and ibuprofen).

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confidence: 99%

Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne

Zhang

Wang

et al. 2022

Org. Lett.

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Palladium‐Catalyzed Stereoselective Cleavage of C−P Bond: Enantioselective Construction of Atropisomers Containing a P‐Stereogenic Center

et al. 2022

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The transition-metal-catalyzed CÀ P bond cleavage has emerged as a powerful tool for the formation of both CÀ C and CÀ P bond. However, the transition-metal-catalyzed stereoselective cleavage of CÀ P bond is still undeveloped. Herein, we report a palladium-catalyzed stereoselective cleavage of CÀ P bond for the construction of P-stereogenic phosphines and stereogenic axis. This protocol enables the quick synthesis of atropisomers bearing a P-stereogenic center in high yields, diastereo-and enantioselectivities of up to 98 % ee, > 25 : 1 dr. The product is able to serve as chiral catalyst in phosphine catalyzed [3+2] cycloaddition of allenoates to imines, showing the great potential of the present methodology.

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Copper‐Catalyzed C4‐selective Carboxylation of Pyridines with CO₂ via Pyridylphosphonium Salts

Tang,

Liu,

Zhang

et al. 2024

Angewandte Chemie

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Pyridine motifs are widespread pharmacophores in many drugs. Installing various substituents through pyridine C−H bond functionalization is significant for new drug design and discovery. Developments of late‐stage functionalization reactions enrich the strategies for selective functionalization of pyridines. However, late‐stage C−H carboxylation of pyridines is a long‐standing challenge, especially selectively carboxylation with CO2 on pyridine motifs. Herein, we describe a practical method for C4−H carboxylation of pyridines via one‐pot C−H phosphination and copper‐catalyzed carboxylation of the resulted phosphonium salts with CO2. The reaction is conducted under mild conditions and compatible with multiple active groups and several pyridine drugs, providing diverse valuable isonicotinic acid compounds, demonstrating the application potential of this strategy.

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Cobalt-catalyzed cross-coupling of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium reagents

Cited by 7 publications

References 50 publications

Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne

Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne

Palladium‐Catalyzed Stereoselective Cleavage of C−P Bond: Enantioselective Construction of Atropisomers Containing a P‐Stereogenic Center

Copper‐Catalyzed C4‐selective Carboxylation of Pyridines with CO₂ via Pyridylphosphonium Salts

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Cobalt-catalyzed cross-coupling of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium reagents

Cited by 7 publications

References 50 publications

Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne

Palladium-Catalyzed Sonogashira Coupling of a Heterocyclic Phosphonium Salt with a Terminal Alkyne

Palladium‐Catalyzed Stereoselective Cleavage of C−P Bond: Enantioselective Construction of Atropisomers Containing a P‐Stereogenic Center

Copper‐Catalyzed C4‐selective Carboxylation of Pyridines with CO2 via Pyridylphosphonium Salts

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Product

Resources

About

Copper‐Catalyzed C4‐selective Carboxylation of Pyridines with CO₂ via Pyridylphosphonium Salts