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

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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

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Publication details

The article was received on 16 Dec 2016, accepted on 06 Feb 2017 and first published on 08 Feb 2017


Article type: Research Article
DOI: 10.1039/C6QO00822D
Citation: Org. Chem. Front., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C6QO00822D

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