Abstract
Palladium(0) catalyzed coupling of β-bromostyrene ( E/ Z = 89/11) with ( E)-(1,2-difluoro-1,2-ethenediyl)bis[tributylstannane], 1, in DMF at room temperature stereospecifically gave only (1 E,3 E,5 E)-3,4-difluoro-1,6-diphenylhexatriene. Similarly, palladium(0) catalyzed coupling of ( E)-ethyl 3-bromoacrylate as the vinyl halide precursor stereospecifically gave (2 E,4 E,6 E)-diethyl-4,5-difluoroocta-2,4,6-trienedioate. This work demonstrates that a non-fluorine-containing vinyl bromide will selectively undergo coupling with 1 and enable the stereospecific preparation of a mixed polyene system. The ( E)-ethyl 3-bromoacrylate coupling with 1 illustrates that mixed functionalized hexatriene systems can be easily accessed via this methodology. The X-ray structure of (2 E,4 E,6 E)-diethyl-4,5-difluoroocta-2,4,6-trienedioate confirmed its structure.
Published Version
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