Endorsing Organic Porous Polymers in Regioselective and Unusual Oxidative C═C Bond Cleavage of Styrenes into Aldehydes and Anaerobic Benzyl Alcohol Oxidation via Hydride Elimination
Debabrat Pathak, Rajiv Khatioda, Himanshu Sharma, Ankur K. Guha, Lakshi Saikia, Bipul Sarma
Abstract
Oxidative cleavage of styrene C═C double bond is accomplished by employing a nitrogen-rich triazine-based microporous organic polymer as an organocatalyst. We report this regioselective reaction as first of its kind with no metal add-ons to afford benzaldehydes up to 92% selectivity via an unusual Wacker-type C═C bond cleavage. Such a reaction pathway is generally observed in the presence of a metal catalyst. This polymer further shows high catalytic efficiency in an anaerobic oxidation reaction of benzyl alcohols into benzaldehydes. The reaction is mediated by a base via the in situ generation of hydride ions. This study is supported by experiments and computational analyses for a free-radical transformation reaction of oxidative C═C bond cleavage of styrenes and a hydride elimination mechanism for the anaerobic oxidation reaction. Essentially, the study unveils protruding applications of metal-free nitrogen-rich porous polymers in organic transformation reactions.