Pd‐catalyzed Three‐component Cross‐coupling of Arylhydrazides with Arylboronic Acids and TFBen: Facile Access to Diaryl Ketones via Denitrogenative Carbonylation

Carbonylation with CO surrogates is one of the most common methods for introduction of carbonyl groups in ketone synthesis. However, arylhydrazides have not been used as an aryl source in this denitrogenative method even though they are cheap and accessible. Here, we report development of palladium catalysis for the three-component reactions of arylboronic acids, CO-surrogates (benzene-1,3,5-triyl triformate), and arylhydrazides under oxygen conditions to produce diaryl ketones. (Hetero)arylhydrazides, as well as (hetero)arylboronic acids are suitable reaction partners, and good functional group compatibility was achieved. This method could be used for streamlined synthesis of diaryl ketones, ketoprofen and fenofibrate. A Pd-catalyzed oxidative carbonylation of arylhydrazines and phenylboronic acids which provides access to diaryl ketones with N2 and H2O as the only byproducts is reported.image