Issue 1, 2022

K2S2O8-mediated acylarylation of unactivated alkenes via acyl radical addition/C–H annulation cascade of N-allyl-indoles with silver cocatalysis

Abstract

A silver-catalyzed, K2S2O8-mediated protocol to access regioselective acylarylation of unactivated alkenes was developed. The reaction between N-allyl-indoles and α-oxocarboxylic acids proceeded smoothly and involved an acyl radical addition/C–H cyclization cascade. The protocol showed a broad substrate scope and good tolerance of functional groups. The reaction proceeded with both internal and terminal alkenes to furnish many functional pyrrolo[1,2-a]indoles bearing the ketone carbonyl group, and this feature also provides the potential to construct structurally complex N-containing heterocycles.

Graphical abstract: K2S2O8-mediated acylarylation of unactivated alkenes via acyl radical addition/C–H annulation cascade of N-allyl-indoles with silver cocatalysis

Supplementary files

Article information

Article type
Research Article
Submitted
20 Jul 2021
Accepted
29 Sep 2021
First published
29 Sep 2021

Org. Chem. Front., 2022,9, 32-38

K2S2O8-mediated acylarylation of unactivated alkenes via acyl radical addition/C–H annulation cascade of N-allyl-indoles with silver cocatalysis

J. Zhang, M. Wu, H. Ju, H. Yang, B. Qian, K. Ding, J. Wu and M. Xie, Org. Chem. Front., 2022, 9, 32 DOI: 10.1039/D1QO01069G

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