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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 6
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Original Articles

Synthesis of Triphenylamine-Modified Arylates and Ketones via Suzuki Coupling Reactions

, , , &
Pages 832-840 | Received 09 Dec 2007, Published online: 25 Feb 2011
 

Abstract

A series of triphenylamine-mdified arylates and ketones were synthesized via Pd-catalyzed Suzuki coupling reaction of triphenylamine boronic acid with aryl bromide. The triphenylamine boronic acid was synthesized by iodization of 4-bromoaniline, Ullmann reaction of 1-bromo-4-iodobenzene with diphenylamine, and boronic acidification of 4-bromotriphenylamine.

ACKNOWLEDGMENTS

This work was financially supported by NSFC 60868001.

Notes

a The reactions were carried out utilizing 3% (mol) of Pd catalyst, 1.0 equiv. of 5, 1.5 equiv. of 6, and 3 equiv. of base under N2.

b Isolated yield.

c The ratio in volume for toluene, ethanol, and H2O was 5:3:1.

d The ratio in volume for ethanol and H2O was 3:1.

e 4 equiv. of base was used.

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