Premium
Palladium‐Catalyzed Intermolecular Three‐Component Coupling of Organic Halides with Alkynes and Alkenes: Efficient Synthesis of Oligoene Compounds
Author(s) -
Shibata Kana,
Satoh Tetsuya,
Miura Masahiro
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700171
Subject(s) - chemistry , catalysis , palladium , fulvene , halide , aryl , intermolecular force , alkyne , organic chemistry , polymer chemistry , medicinal chemistry , alkyl , molecule
The intermolecular three‐component coupling of aryl or vinyl halides, diarylacetylenes, and monosubstituted alkenes effectively proceeds in the presence of palladium acetate, lithium chloride, and sodium bicarbonate as catalyst, promoter, and base, respectively, in aqueous DMF or DMSO to produce the corresponding 1,3‐butadiene or 1,3,5‐hexatriene derivatives. Use of dienyl bromides allows the coupling to afford 1,3,5,7‐octatetraenes. Under the present catalytic conditions, fulvene derivatives are also formed efficiently by the 1:2 coupling of vinyl bromides and diarylacetylenes without adding the alkenes.