Trifluoromethanesulfonyl azide as a bifunctional reagent for metal-free azidotrifluoromethylation of unactivated alkenes.

ABSTRACT: Vicinal trifluoromethyl azides have widespread applications in organic synthesis and drug development. However, their preparation is generally limited to transition-metal-catalyzed three-component reactions. We report here a simple and metal-free method that rapidly provides these building blocks from abundant alkenes and trifluoromethanesulfonyl azide (N₃SO₂CF₃). This unprecedented two-component reaction employs readily available N₃SO₂CF₃ as a bifunctional reagent to concurrently incorporate both CF₃ and N₃ groups, which avoids the use of their expensive and low atom economic precursors. A wide range of functional groups, including bio-relevant heterocycles and amino acids, were tolerated. Application

SUBMITTER: Huang HG 

PROVIDER: S-EPMC8179360 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature