Oxazaborolidinones: Steric Coverage Effect of Lewis Acidic Boron Center in Suzuki–Miyaura Coupling Reactions
Naoki Tsuchiya,
Takaki Nojiri,
Takashi Nishikata
Abstract:It was demonstrated that α‐hydroxycarboxamide is an excellent boron‐protecting group. The reaction between α‐hydroxycarboxamide and organoboronic acids produced stable oxazaborolidinones (OxBs), in which the
‐hybridized boron atom was sterically protected by α‐hydroxycarboxamide. The alkyl groups of the α‐hydroxycarboxamide moiety can dynamically cover the p‐orbital of the
‐hybridized boron center, creating a small space around the boron atom, allowing for smooth transmetalation by a Pd catalyst and easy dep… Show more
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