Double C-H Functionalization in Sequential Order: Direct Synthesis of Polycyclic Compounds by a Palladium-Catalyzed C-H Alkenylation-Arylation Cascade

作者：Ohno Hiroaki^*; Iuchi Mutsumi; Kojima Naoto; Yoshimitsu Takehiko; Fujii Nobutaka; Tanaka Tetsuaki

来源：Chemistry - A European Journal, 2012, 18(17): 5352-5360.

DOI：10.1002/chem.201103819

• C?H bond activation
• domino reactions
• heterocycles
• palladium
• polycycles

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 PCy3 center dot HBF4 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.

• 出版日期2012-4