Litcius/Paper detail

Iron-Catalyzed Asymmetric Decarboxylative Azidation

Kai‐Kai Wang, Yajun Li, Xiaoyan Li, Daliang Li, Hongli Bao

2021Organic Letters40 citationsDOI

Abstract

The first iron-catalyzed asymmetric azidation of benzylic peresters has been reported with trimethylsilyl azide (TMSN3) as the azido source. Hydrocarbon radicals that lack of strong interactions were capable to be enantioselectively azidated. The reaction features good functional group tolerance, high yields, and mild conditions. The chiral benzylic azides can further be used in click reaction, phosphoramidation, and reductive amination, which demonstrate the synthetic values of this reaction.

Topics & Concepts

ChemistryCatalysisAzideFunctional groupTrimethylsilyl azideRadicalCombinatorial chemistryAminationReductive aminationTrimethylsilylOrganic chemistryPolymerSynthesis and Catalytic ReactionsClick Chemistry and ApplicationsOxidative Organic Chemistry Reactions