Hydrogen Bond Donor and Unbalanced Ion Pair Promoter-Assisted Gold-Catalyzed Carbon-Oxygen Cross-Coupling of (Hetero)aryl Iodides with Alcohols

We have developed an efficient gold-catalyzed C-O cross -coupling reaction of (hetero)aryl iodides with primary and secondary alcohols via an AuI-AuIII catalytic cycle. This protocol featured moisture/air insensitivity, simple operation, and excellent functional group tolerance. Good yields were obtained regardless of steric hindrance and electronic factor (electron-rich or poor) of substrates, and the chirality of chiral alcohol starting materials could be preserved. Our protocol worked well for both intermolecular and intramolecular couplings. In addition, the RuPhos ligand was applied to gold-catalyzed cross-couplings. An unbalanced ion pair promoter and hydrogen bond donor solvent might be crucial in this transformation.

Automated summary

We developed an efficient gold-catalyzed C-O cross-coupling reaction of (hetero)aryl iodides with primary and secondary alcohols via an AuI-AuIII catalytic cycle. This protocol exhibited moisture/air insensitivity, simple operation, and excellent functional group tolerance. Good yields were obtained regardless of steric hindrance and electronic factor, and the chirality of chiral alcohol starting materials could be preserved. Our protocol also worked well for both intermolecular and intramolecular couplings. The RuPhos ligand was used as a catalyst for gold-catalyzed cross-couplings. An unbalanced ion pair promoter and hydrogen bond donor solvent might be crucial in this transformation.