ArticleMolecular diversity2019
A highly efficient precatalytic system (XPhos-PdG2) for the Suzuki-Miyaura cross-coupling of 7-chloro-1H-pyrrolo[2,3-c]pyridine employing low catalyst loading.
Article in Molecular diversity, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Discovery of a potent and selective human AC2 inhibitor based on 7-deazapurine analogues of adefovir.Bioorganic & medicinal chemistry · 2023Article
- The Application of Microwaves, Ultrasounds, and Their Combination in the Synthesis of Nitrogen-Containing Bicyclic Heterocycles.International journal of molecular sciences · 2023Review
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9 authors.
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Abstract
An expedient catalytic method for the synthesis of diverse 7-(hetero) aryl-1H-pyrrolo[2,3-c]pyridine analogues via microwave-assisted Suzuki-Miyaura cross-coupling reaction with excellent yield was developed. The method is found to be compatible with various boronic acids and potassium organotrifluoroborates. The formation of highly stable monoligated catalytic species is found to be instrumental in driving the reactions to excellent conversions in Suzuki-Miyaura coupling. Herein, we report our findings on the use of a highly efficient precatalytic system (XPhos-PdG2), containing a bulky monodentate biaryl ligand which allows the rapid reductive elimination to form the true monoligated Pd(0) catalytic species, thereby facilitating the Suzuki coupling reaction of 7-chloro, 6-azaindole system containing unprotected free N-H group with excellent conversions employing low catalyst loadings. Also, we observed that the use of near stoichiometric potassium organotrifluoroborate reagents as alternative coupling partners for boronic acids, which are prone to protodeboronation, resulted in excellent conversions.
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