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. 2020 Jul 17;22(14):5685-5689.
doi: 10.1021/acs.orglett.0c02074. Epub 2020 Jun 30.

The SmI2/TEU--Mediated Cyclization of Unsaturated Halides

Chriss E McDonald  1 , Holly D Bendorf  1 , Joseph R Mauck  1 , Christopher C McAtee  1 , Ahren I Green  1 , David J Ciccarelli  1 , Cassandra A Bendyk  1 , Brandon J Conrad  1 , Angelique T Delgado  1
Affiliations

The SmI2/TEU--Mediated Cyclization of Unsaturated Halides

Chriss E McDonald et al. Org Lett. .

Abstract

The combination of SmI2 and the conjugate base of triethylurea (TEU-) has been shown to favor the cyclization of unsaturated halides over direct reduction to a much greater extent than other SmI2-based reductants. Aryl, heteroaryl, and alkyl halides (X = Br, Cl, F) readily undergo heterocyclization and carbocyclization in the presence of SmI2/TEU-.

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