Oxidation and Bromodehydroxymethylation of Benzylic Alcohols Using NaBrO₃/NaHSO₃ Reagent.

Abstract

Halogenation Halogenation O 0235Oxidation and Bromodehydroxymethylation of Benzylic Alcohols Using NaBrO 3 /NaHSO 3 Reagent. -Treatment of benzylic alcohols bearing para-electron donating substituents having unshared electron-pair with a mixture of sodium bromate and sodium hydrogensulfite results in bromodehydroxymethylation. However, other simple benzylic alcohols are oxidized to form benzaldehydes and benzoic acids. -(LEE, C. K.; KOO, B.-S.; LEE, Y. S.; CHO, H. K.; LEE*, K.-J.; Bull. Korean Chem.

Reinvestigating FeBr3-Catalyzed Alcohol Oxidation with H2O2: Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation?

“…Unexpectedly, further increasing the amount of hydrogen peroxide led to exclusive isolation of dibrominated product 7 in 92% yield. Related demethylene-oxy bromination was also achieved previously by different RBS generated from NaBr/Oxone, LiBr/PIDA, etc., − and our protocol represents a green method for this intriguing transformation. Next, we used CeBr 3 /H 2 O 2 to investigate the oxidation of 1,3-diol ( 1ab ) and β-hydroxy ester ( 1ac ), both of which received less attention in the previous substrate examination.…”