Palladium-catalyzed synthesis of monodisperse, controlled-length, and functionalized oligoanilines

被引:161
作者
Sadighi, JP [1 ]
Singer, RA [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja980052c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The palladium-catalyzed amination of aryl halides, in conjunction with an orthogonal protective group scheme, forms the basis of two routes to oligoaniline precursors. One method consists of a bidirectional chain growth from a symmetric core piece, whereas the other involves a divergent-convergent synthesis of nonsymmetric fragments, followed by coupling to a symmetric core fragment. The oligoaniline precursors are soluble in a variety of common organic solvents and are easily converted to the deprotected oligoanilines. The method allows the preparation of even or odd chain lengths and the incorporation of a variety of functional groups. The synthesis of phenyl-capped heptaaniline through decaaniline, of four end-functionalized octaaniline derivatives, and of phenyl-capped 16-mer and 24-mer is described. The effects of chain length and substitution upon oligomer behavior have been investigated by electronic absorption spectroscopy and cyclic voltammetry.
引用
收藏
页码:4960 / 4976
页数:17
相关论文
共 58 条