Ru Doped Hydrotalcite Catalyzed Borrowing Hydrogen-Mediated N‑Alkylation of Benzamides, Sulfonamides, and Dehydrogenative Synthesis of Quinazolinones

An
efficient Ru doped hydrotalcite catalyzed N-alkylation of benzamides
and sulfonamides with alcohols via borrowing hydrogen catalysis is
illustrated. Various primary alcohols, including benzyl, heteroaryl,
and aliphatic alcohols, were alkylated in good to excellent yields.
To shed light on the mechanistic details, several control studies
and deuterium labeling experiments were performed. Mechanistic studies
underpin that the reaction is going via a borrowing hydrogen pathway
rather than an SN1 type mechanism. The reaction can be
easily scaled up without any detrimental effect on the yield. The
catalyst is also capable of synthesizing quinazolinone directly from
2-aminobenzamide and alcohols. Successful recyclability and high reactivity
highlight the practical applicability of the catalyst.