16291-40-0Relevant articles and documents
Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C-H Activation and Decarboxylation
Yang, Yuzhong,Zhou, Bang,Zhu, Xiaoming,Deng, Guobo,Liang, Yun,Yang, Yuan
, p. 5402 - 5405 (2018)
A novel tandem intermolecular decarboxylative coupling reaction of o-bromobenzoic acids and aryl iodides has been developed. The method affords a range of unsymmetrically triphenylenes and displays unique regioselectivity and broad substrate scope. Mechanistically, palladium/norbornene-catalyzed C-H activation and subsequent double decarboxylative coupling reactions were involved. Moreover, the triphenylenes can also be synthesized from 2-iodobiphenyls and o-bromobenzoic acids under norbornene-free conditions.
Modular metal-free catalytic radical annulation of cyclic diaryliodoniums to access π-extended arenes
Zhu, Daqian,Peng, Hui,Sun, Yameng,Wu, Zhouming,Wang, Yun,Luo, Bingling,Yu, Tiantian,Hu, Yumin,Huang, Peng,Wen, Shijun
supporting information, p. 1972 - 1977 (2021/03/26)
Polycyclic aromatic hydrocarbons (PAHs) are of increasing importance in the advanced material field. Cyclic diaryliodonium salts are non-toxic and environmentally benign arylating reagents. Here, we describe an alkylamine-mediated free radical intramolecular annulation to access PAHs under environmentally friendly conditions. On modulating substituents and their positions in the iodoniums, the free radical reaction controllably underwent three types of cyclization including ring contraction and ring switch to form tricyclic and tetracyclic frameworks of PAHs. Preliminary mechanistic studies implied that alkylamines initiated a radical pathway to complete the cyclization efficiently. Moreover, these acquired products were further converted into diverse complex graphene segments.
Two-in-One Strategy for the Pd(II)-Catalyzed Tandem C-H Arylation/Decarboxylative Annulation Involved with Cyclic Diaryliodonium Salts
Hu, Tao,Xu, Kai,Ye, Zenghui,Zhu, Kai,Wu, Yanqi,Zhang, Fengzhi
supporting information, p. 7233 - 7237 (2019/10/02)
We report here a two-in-one strategy for the Pd(II)-catalyzed tandem C-H arylation/decarboxylative annulation between readily available cyclic diaryliodonium salts and benzoic acids. The carboxylic acid functionality can be used as both a directing group for the ortho-C-H arylation and the reactive group for the tandem decarboxylative annulation. By a step-economical double cross-coupling annulation procedure, the privileged triphenylene frameworks were efficiently constructed, which have potential applications in material chemistry.