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Aldehydes as reducing agents: Reductive alkylation of ketones
Aldehydes are key building blocks in organic synthesis due to their high availability and diverse reactivity.
However, their intrinsic reducing ability remains underutilized. Herein, we illustrate a possibility to use aldehydes
as dual-purpose reagents in redox transformations: as alkylating agents and reductants. This concept is
supported by a ruthenium-catalyzed reductive alkylation of ketones and other nucleophiles using aldehydes. This
operationally simple protocol proceeds under neat conditions without any external reductants providing a
convenient, selective and eco-friendly C–C and C–N bond formation protocol. The utility of the protocol was
illustrated by the synthesis of pharmaceutically relevant scaffolds, including Nabumetone and a derivative of
pregnenolone acetate. Mechanistic experiments along with DFT-calculations were conducted to investigate
mechanism of this transformation.