A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the C (math)N or C (math)C bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitrites and C (math)C bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

Automated summary

This study presents a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids, achieving hydration of triple bonds to carbonyl chemicals. The tetrabutylphosphonium 2-hydroxypyridine demonstrates high efficiency for hydration of nitrites and C–C bond-containing compounds under a CO2 atmosphere, providing excellent yields. This catalytic protocol is simple, green, and efficient, providing a novel way to access carbonyl compounds through triple bond hydration under mild and metal-free conditions.