Synthesis of polybenzyls by Suzuki Pd-catalyzed crosscoupling of boronic acids and benzyl bromides: Model reactions and polyreactions

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Klärner, Claudia ; Greiner, Andreas:
Synthesis of polybenzyls by Suzuki Pd-catalyzed crosscoupling of boronic acids and benzyl bromides: Model reactions and polyreactions.
In: Macromolecular Rapid Communications. Bd. 19 (1998) Heft 12 . - S. 605-608.
ISSN 1521-3927
DOI: https://doi.org/10.1002/(SICI)1521-3927(19981201)19:12<605::AID-MARC605>3.0.CO;2-I

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Abstract

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. (M) over bar(n)'s of 2380 corresponding to a DP of 26 were found based on GPC. No structural defects were detected within the limits of detection.