Reduction of Acetals, Azaacetals and Thioacetals to Ethers

Superbase-Catalyzed anti-Markovnikov Alcohol Addition Reactions to Aryl Alkenes

“…The most direct synthetic route to ethers of this type would be the anti-Markovnikov addition of alcohols to styrene derivatives, a process for which catalysts have long been desired (Figure ). Typically, a three-step hydroboration/oxidation/substitution sequence must be followed in order to achieve the formal anti-Markovnikov addition of alcohols to olefins . Despite impressive developments of Brønsted acid-, metal- and photoredox-catalyzed alcohol addition methodologies, − a general process for the preparation of β-phenethyl ethers remains undeveloped. , In their pioneering work on photoredox-catalyzed alkenol cyclization, the Nicewicz group reported the anti-Markovnikov addition of methanol to trans -anethole, although this intermolecular variant has not been significantly generalized for other substrates …”

Reductive Etherification via Anion-Binding Catalysis

“…Reductive aminations are among the most reliable reactions for amine synthesis due to starting material availability, mild reaction conditions, and broad substrate scope (Figure ). In contrast, the corresponding reductive etherifications are less developed . This is despite the availability of the prerequisite starting materials and the advantages such an approach would offer over classical methods such as the Williamson ether synthesis .…”