Titanium superoxide--a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant.
Titanium superoxide efficiently catalysed the oxidative esterification of aldehydes with alkylarenes or alcohols, under truly heterogeneous conditions, to afford the corresponding benzyl and alkyl esters in excellent yields. Mechanistic studies have established that this "one pot" direct oxidative esterification process proceeds through a radical pathway, proven by a FTIR spectral study of a titanium superoxide-aldehyde complex as well as spin trapping experiments with TEMPO. The intramolecular version of this protocol has been successfully demonstrated in the concise synthesis of 3-butylphthalide, an anti-convulsant drug.
Chemical Engineering & Process Development Division, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, Maharashtra, India. a.sudalai@ncl.res.in.
Soumen
S
Dey
Chemical Engineering & Process Development Division, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, Maharashtra, India. a.sudalai@ncl.res.in.
Sunita K
SK
Gadakh
Chemical Engineering & Process Development Division, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, Maharashtra, India. a.sudalai@ncl.res.in.
A
A
Sudalai
D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000927:Anticonvulsants / Q000138:chemical synthesis; D001572:Benzofurans / Q000138:chemical synthesis; D001593:Benzyl Compounds / Q000737:chemistry*; D004951:Esterification; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry; D013481:Superoxides / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry*
D000438:Alcohols; D000447:Aldehydes; D000927:Anticonvulsants; D001572:Benzofurans; D001593:Benzyl Compounds; D016877:Oxidants; D010545:Peroxides; D013481:Superoxides; C027125:3-n-butylphthalide; D014025:Titanium; C000602361:tert-butyl peroxide