Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination
Fleming, CL; Ashton, TD; Pfeffer, FM
| HERO ID | 3575464 |
|---|---|
| In Press | No |
| Year | 2014 |
| Title | Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination |
| Authors | Fleming, CL; Ashton, TD; Pfeffer, FM |
| Journal | Dyes and Pigments |
| Volume | 109 |
| Page Numbers | 135-143 |
| Abstract | Successful amination of 4-bromo-1,8-naphthalimides with 'lengthy' imide N-functionality has been achieved using a general palladium mediated approach (conventional thermal protocols were suboptimal). Only readily available Pd/ligand combinations were considered and the resulting Buchwald-Hartwig procedure using Pd-2(dba)(3), Xantphos and Cs2CO3 is high yielding, relatively mild (40-80 degrees C, 24 h, yields 50-90%), requires only a modest excess of amine (3.0 equiv) and works equally well with other imide N-substituents. As such, the protocol complements existing methods but is superior for more complex substrates. Herein we compare this Pd mediated approach to the methods most commonly used and further demonstrate its utility by synthesising a number of new, highly fluorescent, 4-aminonaphthalimides. (C) 2014 Elsevier Ltd. All rights reserved. |
| Doi | 10.1016/j.dyepig.2014.05.006 |
| Wosid | WOS:000339695400017 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | Synthesis; 4-Aminonaphthalimide; Buchwald-Hartwig; Amination; Naphthalimide; Palladium |