Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba , Tsukuba, Ibaraki 305-8571, Japan.
Org Lett. 2015 Oct 16;17(20):4984-7. doi: 10.1021/acs.orglett.5b02426. Epub 2015 Sep 29.
Dibenzo[g,p]chrysenes were readily synthesized via the superacid- or TiF4-mediated domino Friedel-Crafts-type cyclization of 1,1-difluoroethenes bearing two biaryl groups, which were easily prepared via the Suzuki-Miyaura coupling of 1,1-difluoro-2,2-diiodoethene or 1-(biphenyl-2-yl)-1-bromo-2,2-difluoroethene. Using this approach, the activation of both vinylic and aromatic C-F bonds was successfully achieved to make new C-C bonds.
二苯并[g,p]苝通过带有两个联苯基团的 1,1-二氟乙烯在超强酸或 TiF4 介导的串联 Friedel-Crafts 型环化反应中很容易合成,而 1,1-二氟-2,2-二碘乙烯或 1-(联苯-2-基)-1-溴-2,2-二氟乙烯的 Suzuki-Miyaura 偶联反应则很容易制备这些联苯基团。通过这种方法,成功地激活了乙烯基和芳族 C-F 键,从而形成了新的 C-C 键。