Kaifeng Chen; Weijie Chen; Fangyuan Chen; Haiman Zhang; Huiying Xu; Zhi Zhou; Wei Yi
Org. Chem. Front., 2021, 8, 4452-4458
https://doi.org/10.1039/D1QO00709B

Abstract

Efficient, mild and metal-free [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes has been realized via a base-mediated tandem [3,3]-sigmatropic rearrangement, which gives direct access to 2-aminobenzofuran derivatives involved in the one-pot cleavage of multiple bonds including C–H, O–N and twofold C–F bonds. The subsequent success of the on-DNA compatible synthesis and the application of the obtained products as potential anticancer agents further demonstrates the versatility of this transformation.