268-77-9Relevant articles and documents
Cascade Oxidative C?H Annulation of Thiophenes: Heck-Type Pathway Enables Concise Access to Thienoacenes
Chen, Xingyu,Yang, Yudong,Han, Weiguo,Huang, Quan,Huang, Zhenmei,You, Jingsong
, p. 12371 - 12375 (2021/05/03)
The pursuit of efficient synthetic route to thienoacenes represents an appealing yet challenging task in the fields of both organic synthetic chemistry and organic functional materials. In this work, we disclose a rhodium-catalyzed cascade C?H annulation of phenacyl phosphoniums with (benzo)thiophenes via a Heck-type pathway to provide a new class of planar thienoacenes, which involves the formation of three Caryl-Caryl bonds and one Caryl?O bond in a single operation. The neutral S,O-heteroacenes exhibit superior stability and adopt a herringbone-like packing mode with efficient π–π stacking in the crystals, suggesting their potential in organic semiconducting materials. This work first exemplifies the superiority of cascade oxidative C?H annulation involving a Heck-type pathway in the development of concise access to heteroacenes.
Palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehydes
Lei, Lan,Wu, Ping,Liu, Zhuqing,Lou, Jiang
supporting information, (2021/02/16)
The palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehyde derivatives was achieved utilizing 2-dimethylaminoethylamine as a novel transient directing group. The γ-C(sp3)–H arylation reaction efficiently afforded a variety of arylated o-alkylbenzaldehydes and polycyclic aromatic hydrocarbons (PAHs) in one pot, exhibiting high functional group tolerance with broad substrate scope. The aliphatic diamine auxiliary represents a simple, inexpensive, readily available, and removable directing group for C–H activation. The resultant o-benzylbenzaldehyde products could be diversely transformed into potentially important synthetic intermediates under mild conditions.
Synthesis of annulated arenes and heteroarenes by hydriodic acid and red phosphorus mediated reductive cyclization of 2-(Hetero)aroylbenzoic acids or 3-(Hetero)arylphthalides
Rafiq, Settu Muhamad,Mohanakrishnan, Arasambattu K.
supporting information, p. 362 - 370 (2017/02/10)
Annulated arenes and hetarenes were prepared in good to very good yields by hydriodic acid/red phosphorus mediated reductive cyclization of 3-(hetero)aryl phthalides. The reductive cyclization also proceeded successfully with 2-aroylbenzoic acids and 2-aroylnaphthoic acids.