Issue 6, 2017

Iodine(iii)-induced regioselective carbocyclization of terminal alkynes: a facile approach to prepare 1,1-diiodomethylene substituted cyclic compounds

Abstract

An iodine(III)-induced regioselective intramolecular carbocyclization of functionally substituted terminal alkynes is reported. A range of 1,1-diiodomethylene substituted cyclic compounds were prepared by using iodide salts as the iodine source to replace the normally used electrophilic I2, NIS or ICl. The use of 2,2,2-trifluoroethanol as a solvent is essential for the generation of reactive iodine(III) species. The resulting diiodomethylene substituted cyclic compounds can be readily converted to tetra-substituted alkenes through transition metal-catalyzed coupling reactions.

Graphical abstract: Iodine(iii)-induced regioselective carbocyclization of terminal alkynes: a facile approach to prepare 1,1-diiodomethylene substituted cyclic compounds

Supplementary files

Article information

Article type
Research Article
Submitted
16 Dec 2016
Accepted
06 Feb 2017
First published
08 Feb 2017

Org. Chem. Front., 2017,4, 1005-1010

Iodine(III)-induced regioselective carbocyclization of terminal alkynes: a facile approach to prepare 1,1-diiodomethylene substituted cyclic compounds

Z. Wang, J. Zhong, C. Zheng and R. Fan, Org. Chem. Front., 2017, 4, 1005 DOI: 10.1039/C6QO00822D

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