Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

Beilstein Journal of Organic Chemistry

Ludovic Favereau¹  Liliia Moshniaha²  Marcin Stępień²  Piotr J. Chmielewski²  Marika Żyła-Karwowska²  Joanna Cybińska² 

[1] Université Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, F-35000 Rennes, France;Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland;

关键词: donor–acceptor systems;    double c–h bond activation;    helicenes;    pyrroles;   

DOI  :  10.3762/bjoc.16.81

来源: DOAJ

【 摘 要 】

Boomerang-shaped bipyrroles containing donor–acceptor units were obtained through a tandem palladium-mediated reaction consisting of a cyclization step, involving double C–H bond activation, and a double α-oxygenation. The latter reaction can be partly suppressed for the least reactive systems, providing access to α-unsubstituted boomerangs for the first time. These “α-free” systems are highly efficient fluorophores, with emission quantum yields exceeding 80% in toluene. Preliminary measurements show that helicene-like boomerangs may be usable as circularly polarized luminescent materials.

【 授权许可】

Unknown