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.