Metal‐Free Chemoselective Oxidative Dehomologation or Direct Oxidation of Alcohols: Implication for Biomass Conversion. Issue 3 (18th December 2015)

• Record Type: Journal Article
• Authors: Kim, Sun Min; Shin, Hun Yi; Kim, Dong Wan; Yang, Jung Woon
• Is Part Of: ChemSusChem. Volume 9:Issue 3(2016:Feb.)
• Page Start: 241
• Page End: 245
• Publication Date: 2015-12-18
• Subjects: biomass conversion -- chemoselectivity -- dehomologation -- lignin -- oxidation; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201501359
• Languages: English
• ISSNs: 1864-5631

Abstract

Abstract: A transition metal‐free, chemoselective reaction was performed using the sodium tert ‐butoxide–oxygen (NaO t Bu–O2 ) system, resulting in either oxidative dehomologation or direct oxidation of alcohols. In particular, the newly developed protocol may be used to predict the major product formed, which depends on alkyl chain length of the alcohols and reaction conditions. The rational mechanism of this transformation was also demonstrated by performing an 18 O isotopic labelling experiment. This protocol presents a straightforward method for biomass conversion of a lignin model compound to phenol and benzoic acid. Abstract : No metals : A transition‐metal‐free chemoselective reaction (either oxidative dehomologation or direct oxidation) of alcohols is performed using the sodium tert ‐butoxide–oxygen system. In particular, this protocol may be used to predict the major product formed, which depends on alkyl chain length of the alcohols and reaction conditions. We also present a straightforward method for the conversion of lignin (as biomass model compound) to phenol and benzoic acid.