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

Jeong-Yu Son, Jonghye Kim, Sang Hoon Han, Sung Hong Kim and Phil Ho Lee*

*Department of Chemistry, Kangwon National University, Chuncheon 24341, Republic of Korea, Email: phleekangwon.ac.kr

J.-Y. Son, J. Kim, S. H. Han, S. H. Kim, P. H. Lee, Org. Lett., 2016, 18, 5408-5411.

DOI: 10.1021/acs.orglett.6b02805 (free Supporting Information)


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Abstract

A rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with aliphatic, aromatic, and heteroaromatic alkenes enables a regioselective synthesis of a wide range of dihydrothiophenes. A subsequent addition of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) provides thiophenes. The present method offers broad substrate scope, wide functional group compatibility, and high regioselectivity.

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Key Words

S-heteroycles


ID: J54-Y2016