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Synthesis of 2,3-dihydrothiophenes

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


A formal (3+2)-cycloaddition of donor-acceptor cyclopropanes and ammonium thiocyanate catalyzed by Yb(OTf)3 delivers 2-amino-4,5-dihydrothiophenes in very good yields. A broad range of functional groups is tolerated.
A. Jacob, P. Barkawitz, I. A. Andreev, N. K. Ratmanova, I. V. Trushkov, D. B. Werz, Synlett, 2021, 32, 901-904.