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Org Lett. 2015 May 01;17(9):2126-9. doi: 10.1021/acs.orglett.5b00716. Epub 2015 Apr 17.

Gallium(III)-Promoted Halocyclizations of 1,6-Diynes.

Organic letters

Kyle R Strom, Anna C Impastato, Kenneth J Moy, Adrian J Landreth, John K Snyder

Affiliations

  1. Department of Chemistry Boston University, Boston, Massachusetts 02215, United States.

PMID: 25885017 DOI: 10.1021/acs.orglett.5b00716

Abstract

Cyclization of 1,6-diynes promoted by stoichiometric Ga(III) halides produces vinyl halides in good to excellent yields. Under acidic conditions, initially formed iodocyclization products undergo in situ Friedel-Crafts cyclizations, giving access to iodoindenopyridines. Application of the vinyl halides in cross-coupling reactions has been explored, and mechanistic aspects of the cyclization are discussed.

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