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Org Lett. 2016 Oct 21;18(20):5408-5411. doi: 10.1021/acs.orglett.6b02805. Epub 2016 Oct 10.

Regioselective Synthesis of Dihydrothiophenes and Thiophenes via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes.

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1
Department of Chemistry, Kangwon National University , Chuncheon 24341, Republic of Korea.
2
Analysis Research Division Daegu Center, Korea Basic Science Institute , Daegu 41566, Republic of Korea.

Abstract

A method for the regioselective synthesis of a wide range of dihydrothiophenes was developed from the rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with aliphatic, aromatic, and heteroaromatic alkenes. Tandem rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with alkenes followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation was also demonstrated for the one-pot regioselective synthesis of various thiophenes. Advantages of the present method include a broad substrate scope, wide functional group compatibility, and high regioselectivity.

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