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Palladium‐Catalyzed Syntheses of Polyethynyl‐Substituted 2,2′‐Bithiophenes
Author(s) -
Dahlmann Uwe,
Neidlein Richard
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790318
Subject(s) - chemistry , acetylene , catalysis , palladium , trimethylsilyl , organic chemistry , medicinal chemistry
The syntheses of polyethynyl‐substituted 2,2′‐bithiophenes 2 and related 5,5′‐dicarbaldehyde derivatives 1 are described. The treatment of easily available polybrominated 2,2′‐bithiophenes 3 and 2,2′‐bithiophene‐5,5′‐dicarbaldehydes 4 with phenyl or (trimethylsilyl)acetylene in the presence of Pd II and Cu I in (i‐Pr) 2 NH yields substituted polyethynyl‐2,2′‐bithiophene compounds. The Me 3 Si protecting groups can be removed by protodesilylation under basic conditions to give the corresponding terminal ethynyl groups. These polyethynyl‐bithiophenes could be interesting precursors for the synthesis of macrocycles with interesting properties.