MeBOMA

CAS 7470-08-8, Cat. No EN300-45159795

Protection group for boronic acids

MeBOMA is a new protection group for boronic acids. MeBOMA-Protected boronic acids have shown to be a shelf-stable compound that is solid, soluble in the THF and chloroform, and can survive in high temperatures (150℃ in a vacuum). This PG is stable under neutral and base conditions and even has prolonged stability in soft acidic conditions at lower temperatures, below 20℃, but with higher temperatures, it is deprotecting. The MeBOMA protecting group was effective in masking the boronates during Suzuki−Miyaura cross-coupling, even under aqueous basic conditions, allowing for selective cross-coupling. MeBOMA tolerates the cleavage of a methyl ester to form carboxylic acid (base conditions) and strong nucleophilic organometallic bases such as n-BuLi, allowing lithium−halogen exchange reactions to take place at -78℃ in high yield. MeBOMA boronates were also found to be stable to hydroxydeboronation with peroxides under conditions that would convert most other boron species into their corresponding phenols.

Synonyms: 2-({[(2-hydroxy-5-methylphenyl)methyl](methyl)amino}methyl)-4-methylphenol, 2,2′-[(Methylimino)bis(methylene)]bis[phenol]