Synergetic catalysis of Se and Cu allowing diethoxylation of halomethylene ketones using O2 as the mild oxidant

PhSe(O)OH/Cu(OAc)(2)-Catalyzed diethoxylation of halomethylene ketones for the construction of useful alpha-keto acetals was developed. Synergetic catalysis of Se and Cu allowed the utilization of molecular oxygen as a safe oxidant instead of explosive hydrogen peroxide. The easily accessible bromo-containing substrates could release HBr during the reaction, which promoted the key enol intermediate to avoid the use of acidic additives and allow the reaction to occur under mild conditions.

Automated summary

The diethoxylation of halomethylene ketones for the synthesis of valuable alpha-keto acetals was achieved using PhSe(O)OH/Cu(OAc)(2) catalysis, enabling the use of molecular oxygen instead of hazardous hydrogen peroxide. The presence of easily accessible bromo-containing substrates facilitated the release of HBr during the reaction, promoting the formation of key enol intermediates and allowing the reaction to proceed under mild conditions.