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A New Efficient Synthesis of the Stilbenoid Laser Dyes BPS and Stilbene I by Palladium‐Catalyzed Coupling of Ethene with Bromoarenes
Author(s) -
Rümper Jörg,
Sokolov Viktor V.,
Rauch Karsten,
Meijere Armin De
Publication year - 1997
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19971300905
Subject(s) - chemistry , palladium , catalysis , salt (chemistry) , coupling (piping) , combinatorial chemistry , organic chemistry , mechanical engineering , engineering
The palladium‐catalyzed coupling of ethene with 4‐bromobiphenyl and 4′‐bromo‐4‐biphenylsulfonic acid permits a facile one‐pot preparation of the laser dyes ( E )−4,4′‐diphenylstilbene (BPS, 3) and bis(triethylammonium) ( E )−4,4′diphenylstilbene‐4″,4″‐disulfonate ( 6 ) in diastereomerically pure form on a multigram scale, with yields of 69 and 64%, repectively. The latter can easily be transformed to its dipotassium salt 7 , the Stilbene I dye.