Palladium(II)-catalyzed direct annulation of 2-chloronicotinaldehyde with 2-bromothiophenol via novel C(formyl)-C(aryl) coupling strategy

Morja, Mayur I.; Chauhan, Prakashsingh M.; Chikhalia, Kishor H.

doi:10.1007/s11164-021-04536-1

Res Chem Intermed

2021

DOI: 10.1007/s11164-021-04536-1

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Palladium(II)-catalyzed direct annulation of 2-chloronicotinaldehyde with 2-bromothiophenol via novel C(formyl)-C(aryl) coupling strategy

Mayur I. Morja

Prakashsingh M. Chauhan

Kishor H. Chikhalia

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2024

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Cited by 6 publications

References 55 publications

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Palladium(II)‐katalysierte nicht‐dirigierte late‐stage C(sp²)−H Deuterierung von Heteroaromaten ermöglicht über einen Multi‐Substrat‐Screening‐Ansatz

Dey,

Kaltenberger,

van Gemmeren

2024

Angewandte Chemie

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The importance of deuterium labelling in a variety of applications, ranging from mechanistic studies to drug‐discovery, has spurred immense interest in the development of new methods for its efficient incorporation in organic, and especially in bioactive molecules. The five‐membered heteroarenes at the center of this work are ubiquitous motifs in bioactive molecules and efficient methods for the deuterium labelling of these compounds are therefore highly desirable. However, the profound differences in chemical properties encountered between different heteroarenes hamper the development of a single set of broadly applicable reaction conditions, often necessitating a separate optimization campaign for a given type of heteroarene. In this study we describe the use of a multi‐substrate screening approach to identify optimal reaction conditions for different classes of heteroarenes from a minimal number of screening reactions. Using this approach, four sets of complementary reaction conditions derived from our dual ligand‐based palladium catalysts for nondirected C(sp2)–H activation were identified, that together enable the deuteration of structurally diverse heteroarenes, including bioactive molecules.

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Palladium(II)‐katalysierte nicht‐dirigierte late‐stage C(sp²)−H Deuterierung von Heteroaromaten ermöglicht über einen Multi‐Substrat‐Screening‐Ansatz

Dey,

Kaltenberger,

van Gemmeren

2024

Angewandte Chemie

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Palladium(II)‐Catalyzed Nondirected Late‐Stage C(sp²)−H Deuteration of Heteroarenes Enabled Through a Multi‐Substrate Screening Approach

Dey,

Kaltenberger,

van Gemmeren

2024

Angew Chem Int Ed

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Palladium(0)-catalyzed aryne annulation: a powerful strategy for the synthesis of thio-bridged compounds

Morja¹,

Chikhalia

2022

Mol Divers

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Palladium(II)-catalyzed direct annulation of 2-chloronicotinaldehyde with 2-bromothiophenol via novel C(formyl)-C(aryl) coupling strategy

Cited by 6 publications

References 55 publications

Palladium(II)‐katalysierte nicht‐dirigierte late‐stage C(sp²)−H Deuterierung von Heteroaromaten ermöglicht über einen Multi‐Substrat‐Screening‐Ansatz

Palladium(II)‐katalysierte nicht‐dirigierte late‐stage C(sp²)−H Deuterierung von Heteroaromaten ermöglicht über einen Multi‐Substrat‐Screening‐Ansatz

Palladium(II)‐Catalyzed Nondirected Late‐Stage C(sp²)−H Deuteration of Heteroarenes Enabled Through a Multi‐Substrate Screening Approach

Palladium(0)-catalyzed aryne annulation: a powerful strategy for the synthesis of thio-bridged compounds

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Palladium(II)-catalyzed direct annulation of 2-chloronicotinaldehyde with 2-bromothiophenol via novel C(formyl)-C(aryl) coupling strategy

Cited by 6 publications

References 55 publications

Palladium(II)‐katalysierte nicht‐dirigierte late‐stage C(sp2)−H Deuterierung von Heteroaromaten ermöglicht über einen Multi‐Substrat‐Screening‐Ansatz

Palladium(II)‐katalysierte nicht‐dirigierte late‐stage C(sp2)−H Deuterierung von Heteroaromaten ermöglicht über einen Multi‐Substrat‐Screening‐Ansatz

Palladium(II)‐Catalyzed Nondirected Late‐Stage C(sp2)−H Deuteration of Heteroarenes Enabled Through a Multi‐Substrate Screening Approach

Palladium(0)-catalyzed aryne annulation: a powerful strategy for the synthesis of thio-bridged compounds

Contact Info

Product

Resources

About

Palladium(II)‐katalysierte nicht‐dirigierte late‐stage C(sp²)−H Deuterierung von Heteroaromaten ermöglicht über einen Multi‐Substrat‐Screening‐Ansatz

Palladium(II)‐katalysierte nicht‐dirigierte late‐stage C(sp²)−H Deuterierung von Heteroaromaten ermöglicht über einen Multi‐Substrat‐Screening‐Ansatz

Palladium(II)‐Catalyzed Nondirected Late‐Stage C(sp²)−H Deuteration of Heteroarenes Enabled Through a Multi‐Substrate Screening Approach