Litcius/Paper detail

Copper Catalyzed‐TBHP/DTBP Promoted C(sp<sup>2</sup>)−H Bond Scission of Aldehydes: An Approach to Transform Aldehyde to Esters

Neha Dagar, Swati Singh, Sudipta Raha Roy

2021Asian Journal of Organic Chemistry14 citationsDOI

Abstract

Abstract The direct oxidative C(sp 2 )−H functionalization represents a step and atom economical approach for the utilization of aldehyde as promising acyl surrogates. A mild and practical copper catalyzed‐TBHP/DTBP promoted esterification of aldehydes in the presence of alkyl halides and alcohols has been developed. This strategy relies on naturally abundant aldehydes as acyl precursors, which can further couple with readily available alkyl halides/alcohols to transform into esters. Preliminary mechanistic investigations reveal that aldehyde in the presence of tert ‐butoxy radical transforms into acyl radical. This protocol exhibits a broad substrate scope along with wide functional group compatibility and is applicable to a wide range of aldehydes, including challenging aliphatic aldehydes to undergo the C(sp 2 )−H bond scission to furnish the desired esters in good to excellent yields.

Topics & Concepts

ChemistryAldehydeAlkylBond cleavageCatalysisHalideOrganic chemistryCombinatorial chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions