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Abstract
The azido group occupies an important position in modern organic chemistry, broadly used as amine surrogates and as anchors in bioconjugation. Despite their importance, examples of selective direct azidation of inert C(sp³)-H bonds remain limited and often require strong oxidative conditions. Herein, we highlight the use of O-acyl oximes and N-acyloxy imidates as directing groups for the selective iron-catalysed azidation of C(sp³)-H bond with trimethylsilyl azide, giving access to various γ-azido ketones and β-azido alcohols in moderate to excellent yields. The iron catalyst is assumed to play a dual role in these catalytic processes: as a reductant to generate the reactive iminyl and imidate radicals, respectively, and as a redox centre to mediate the azido transfer to the translocated carbon radical.
Highlights
Since its discovery, the azido group has evolved to become an important functional group in organic chemistry. In addition to their high energetic properties, azides have emerged as versatile synthetic building blocks[1] (Fig. 1), playing an important role in the synthesis of complex molecules as a latent amino group
1.1 Aliphatic C–H Azidation One of the most reliable methods to access aliphatic azides involves a nucleophilic substitution of alkylhalides by alkali azides, thereby requiring pre-functionalised organic substrates
Despite the recent development of C–H functionalisation methodologies, reports for the direct azidation of aliphatic C–H bonds remain limited to oxidative conditions
Summary
The azido group has evolved to become an important functional group in organic chemistry. Alexandre is a PhD student in the same group working on the development of new remote C–H functionalisation strategies. Despite the recent development of C–H functionalisation methodologies, reports for the direct azidation of aliphatic C–H bonds remain limited to oxidative conditions.
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