Deoxygenation of
alcohols is an important tool in the repertoire
of defunctionalization methods in modern synthetic chemistry. We report
the base-metal-catalyzed direct deoxygenation of benzylic and aliphatic
primary alcohols via oxidative dehydrogenation/Wolff–Kishner
reduction. The reaction is catalyzed by a well-defined PNP pincer
complex of Earth-abundant manganese, evolving H2, N2, and water as the only byproducts.
New atom-economical, environmental friendly, direct oxidative intermolecular processes of amination and hydrazination of nonprefunctionalized arenes were developed. The products were formed in a good regioselective manner under organocatalytic conditions at ambient temperature.
A straightforward substitution of silicon-bonded methoxy groups by a lithium amide leading to aminomethoxysilanes is presented. DFT calculations allow thermodynamic insight into the unusual equilibrium conditions. The applicability of N,O-functionalised organosilanes is exemplified by the convenient synthesis of an unsymmetrical methoxydisiloxane.
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