Issue 28, 2018

An efficient iodine pentoxide-triggered iodocarbocyclization for the synthesis of iodooxindoles in water

Abstract

An efficient iodocarbocyclization of alkenes for the synthesis of iodooxindoles has been developed. This reaction proceeds in a chemoselective manner and shows excellent tolerance of various functional groups, including a chemosensitive hydroxymethyl group. Nonmetal inorganic iodine pentoxide was used as both the oxidant and iodine source, making this protocol very practical. On the basis of experimental observations, a plausible electrophilic reaction mechanism was proposed.

Graphical abstract: An efficient iodine pentoxide-triggered iodocarbocyclization for the synthesis of iodooxindoles in water

Supplementary files

Article information

Article type
Paper
Submitted
14 May 2018
Accepted
28 Jun 2018
First published
28 Jun 2018

Org. Biomol. Chem., 2018,16, 5197-5202

An efficient iodine pentoxide-triggered iodocarbocyclization for the synthesis of iodooxindoles in water

M. Zhang, X. Wang, M. Gong, L. Chen, W. Shi, S. He, Y. Jiang and T. Chen, Org. Biomol. Chem., 2018, 16, 5197 DOI: 10.1039/C8OB01130C

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