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Rhodium‐Catalyzed Annulative Coupling of 3‐Phenylthiophenes with Alkynes Involving Double C‐H Bond Cleavages
Author(s) -
Iitsuka Tomonori,
Hirano Koji,
Satoh Tetsuya,
Miura Masahiro
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303847
Subject(s) - rhodium , thiophene , conjugated system , chemistry , catalysis , double bond , moiety , coupling reaction , ring (chemistry) , polymer chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , photochemistry , organic chemistry , polymer
Double CH bond activation took place efficiently upon treatment of 3‐phenylthiophenes with alkynes in the presence of a rhodium catalyst and a copper salt oxidant to form the corresponding naphthothiophene derivatives. Dehydrogenative coupling with alkenes was also found to occur on the phenyl moiety rather than the thiophene ring. These reactions provide straightforward synthetic methods for π‐conjugated molecules involving a thiophene unit from readily available, simple building blocks.