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

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.

Keywords:

• Arylates
• ketones
• Suzuki-coupling
• triphenylamine
• triphenylamine boronic acid

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.