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Synthesis of polybenzyls by Suzuki Pd‐catalyzed crosscoupling of boronic acids and benzyl bromides: Model reactions and polyreactions
Author(s) -
Klärner Claudia,
Greiner Andreas
Publication year - 1998
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/(sici)1521-3927(19981201)19:12<605::aid-marc605>3.0.co;2-i
Subject(s) - yield (engineering) , palladium , catalysis , boronic acid , chemistry , benzene , suzuki reaction , coupling reaction , combinatorial chemistry , organic chemistry , reaction conditions , medicinal chemistry , materials science , metallurgy
The palladium‐catalyzed crosscoupling reaction of boronic acids and benzyl bromides can be used successfully for the preparation of benzyls in high yield. This C‐C coupling reaction was optimized for the synthesis of polybenzyls by model reactions. Different reaction channels were observed here with meta ‐ and para ‐bis(bromomethyl)benzenes. The main product with 1,3‐bis(chloromethyl)benzene was the corresponding 1,3‐dibenzylbenzene, but the main product with 1,4‐bis(chloromethyl)benzene was the corresponding biaryl resulting from homocoupling of aromatic boronic acid. 1.3‐Linked polybenzyls were synthesized based on the results of the model reactions. M̄ n 's of 2 380 corresponding to a DP of 26 were found based on GPC. No structural defects were detected within the limits of detection.