Synthesis of Unsymmetrical Triarylamines for Photonic Applications via One-Pot Palladium-Catalyzed Animations

Chemistry of Materials

Volumn 9, Issue 12, 1997, Pages 3231-3235

  Thayumanavan, S ^a   Barlow, Stephen ^a   Marder, Seth R ^a,b  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000754040     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm970567n     Document Type: Article

References (24)

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20. The formation of 8 was judged by the disappearance of the arylamine 6. The compound 4,4′-bis(m-tolylamino)biphenyl has also been synthesized independently and was cospotted with appropriate reaction mixtures and starting materials to judge the completion of the first step of the reaction.
21. In the general methodology depicted in Scheme 3, the second aryl bromide can be added in excess. However, in the alternate pathway the second aryl bromide 7 should be exactly 0.5 equiv relative to the arylamine to achieve optimal yields.
22. It is not clear to us why the cyano substituent at the meta position also inhibits the reaction (entry 9).
23. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 8232 and references therein.
24. From a synthetic viewpoint, this problem can be circumvented by having the electron-donating functional group on the starting arylamine 6 instead of the aryl bromide 9 (compare entries 6 and 7).