Synthesis of 3-aryl-1-phosphinoimidazo[1,5-]pyridine ligands for use in Suzuki-Miyaura cross-coupling reactions

3-Aryl-1-phosphinoimidazo[1,5- a ]pyridine ligands were synthesized from 2-aminomethylpyridine as the initial substrate via two complementary routes. The first synthetic pathway underwent the coupling of 2-aminomethylpyridine with substituted benzoyl chlorides, followed by cyclization, iodination an...

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Bibliographic Details
Published in:RSC advances 2021-08, Vol.11 (45), p.28347-28351
Main Authors: Tran, Ryan Q, Dinh, Long P, Jacoby, Seth A, Harris, Nekoda W, Swann, William A, Williamson, Savannah N, Semsey, Rebecca Y, Yet, Larry
Format: Article
Language:English
Subjects:
Aldehydes
Aromatic compounds
Chemical reactions
Chemistry
Cross coupling
Iodination
Ligands
Palladium
Phosphorus
Pyridines
Substrates
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Summary:3-Aryl-1-phosphinoimidazo[1,5- a ]pyridine ligands were synthesized from 2-aminomethylpyridine as the initial substrate via two complementary routes. The first synthetic pathway underwent the coupling of 2-aminomethylpyridine with substituted benzoyl chlorides, followed by cyclization, iodination and palladium-catalyzed cross-coupling phosphination reactions sequence to give our phosphorus ligands. In the second route, 2-aminomethylpyridine was cyclized with aryl aldehydes, followed by the iodination and palladium-catalyzed cross-coupling phosphination reactions to yield our phosphorus ligands. The 3-aryl-1-phosphinoimidazo[1,5- a ]pyridine ligands were evaluated in palladium-catalyzed sterically-hindered biaryl and heterobiaryl Suzuki-Miyaura cross-coupling reactions. 3-Aryl-1-phosphinoimidazo[1,5- a ]pyridine ligands were synthesized from 2-aminomethylpyridine as the initial substrate via two complementary routes and were evaluated in the Suzuki-Miyaura cross-coupling reactions.
ISSN:2046-2069
2046-2069
DOI:10.1039/d1ra05417a