Issue 14, 2016

Sunlight-promoted cyclization versus decarboxylation in the reaction of alkynoates with N-iodosuccinimide: easy access to 3-iodocoumarins

Abstract

A sunlight-initiated radical conversion of aryl alkynoates to 3-iodocoumarins has been achieved using N-iodosuccinimide as the iodine source without the use of a catalyst or additive. Experimental, X-ray analysis, and computational studies indicate that the reaction under sunlight proceeds through iodination, spirocyclization and ring expansion to form the kinetic product. The sunlight-driven reaction provides a green pathway to especially valuable 3-halocoumarins derivatives.

Graphical abstract: Sunlight-promoted cyclization versus decarboxylation in the reaction of alkynoates with N-iodosuccinimide: easy access to 3-iodocoumarins

Supplementary files

Article information

Article type
Communication
Submitted
12 Apr 2016
Accepted
22 Jun 2016
First published
23 Jun 2016

Green Chem., 2016,18, 3935-3939

Sunlight-promoted cyclization versus decarboxylation in the reaction of alkynoates with N-iodosuccinimide: easy access to 3-iodocoumarins

S. Ni, J. Cao, H. Mei, J. Han, S. Li and Y. Pan, Green Chem., 2016, 18, 3935 DOI: 10.1039/C6GC01027J

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