140473-84-3Relevant articles and documents
Double C-H functionalization in sequential order: Direct synthesis of polycyclic compounds by a palladium-catalyzed C-H alkenylation-arylation cascade
Ohno, Hiroaki,Iuchi, Mutsumi,Kojima, Naoto,Yoshimitsu, Takehiko,Fujii, Nobutaka,Tanaka, Tetsuaki
supporting information; experimental part, p. 5352 - 5360 (2012/05/20)
Palladium-catalyzed cascade C-H alkenylation and arylation provides convenient access to polycyclic aromatic compounds. Treatment of 3-bromoaniline derivatives bearing a bromocinnamyl group on the nitrogen atom with a catalytic amount of [Pd(OAc)2] and PCy3aHBF4 in the presence of Cs2CO3 in dioxane affords naphthalene-fused indole derivatives in good yields. This double cyclization reaction is also applicable to heterocyclic substrates, giving fused indoles containing a heteroaromatic ring such as dibenzofuran, dibenzothiophene, carbazole, indole, or benzofuran through heterocyclic C-H arylation. When using a 2,6-unsubstituted aniline derivative, the first C-H arylation preferentially proceeds at the more hindered position of the aniline ring.
