Categories: Synthesis of S-Heterocycles >
Synthesis of 2,3-dihydrothiophenes
Recent Literature
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.