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Synthesis of Amido-N-imidazolium Salts and their Applications as Ligands in Suzuki–Miyaura Reactions: Coupling of Hetero- aromatic Halides and the Synthesis of Milrinone and Irbesartan

✍ Scribed by Manian Rajesh Kumar; Kyungho Park; Sunwoo Lee

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
301 KB
Volume
352
Category
Article
ISSN
1615-4150

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✦ Synopsis

A new catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki-Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki-Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to give the corresponding aryl compounds in high yield. The yield was increased with increasing steric bulkiness of the substituted group. Especially, 1-(2,6-diisopropylphenyl)-3-N-(2,4,6-tri-tert-butylphe-nylacetamido)imidazolium bromide (4bc) exhibited 850,000 TON in the coupling reaction of 2-bromopyridine and phenylboronic acid. In addition, pharmaceutical compounds such as milrinone and irbesartan were synthesized via Suzuki-Miyaura coupling using sterically bulky, amido-N-imidazolium salt (4bc) as a ligand.

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