C-C bond formation via C-H bond activation: catalytic arylation and alkenylation of alkane segments.
C-C bond formation via C-H bond activation: catalytic arylation and alkenylation of alkane segments.
复制标题
通过 C-H 键活化形成 C-C 键：烷烃链段的催化芳基化和烯基化。
DOI：
10.1021/ja027891q
复制
发表时间：
2002
影响因子：
15
通讯作者：
Sames,Dalibor
中科院分区：
文献类型：
--
作者：
Sezen,Bengü;Franz,Roberto;Sames,Dalibor
A new system for catalytic arylation and alkenylation of alkane segments has been developed. Theortho-tert-butylaniline substrates and 2-pivaloylpyridine may be arylated and alkenylated at thetert-butyl group, while no functionalization occurred at more reactive C−H and other bonds. Arylation and alkenylation of these substrates are achieved in the presence of Ph2Si(OH)Me and Ph−CHCH−Si(OH)Me2, respectively, and the catalytic amount of Pd(OAc)2and stoichiometric oxidant (Cu(OAc)2, 2 equiv) in DMF. In contrast, theortho-i-propylaniline substrate underwent cyclopalladation, but no arylation product was obtained. Complex compound14was synthesized via tandem arylation-alkenylation oftert-butylaniline11. We hypothesize that the high selectivity of this system stems from the confluence of directing effect of the Schiff base or pyridine moiety and unique reactivity properties of a phenyl-palladium acetate species (Ph-Pd-OAc·Ln).
