Construction and Functionalization of Highly Strained N-Doped Zigzag Hydrocarbon Belts  

作　　者：Ming Xie Shuo Tong Mei-Xiang Wang 

机构地区：[1]MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology,Department of Chemistry,Tsinghua University,Beijing 100084

出　　处：《CCS Chemistry》2023年第1期117-123,共7页中国化学会会刊（英文）

基　　金：We thank the National Natural Science Foundation of China(grant nos.22050005,21732004,and 21821001);the Tsinghua University Initiative Scientific Research Program(grant no.2019Z07L01004)for generous financial support.

摘　　要：Recent years have witnessed breakthroughs in the study of zigzag hydrocarbon belts.However,the synthesis of heterocycle-containing zigzag molecular belts remains very rare and challenging despite their interesting structures and potential applications in chemistry and materials science.Here,we report the expeditious construction of a highly strained belt[4]arene[4](1,4-dihydropyridine)structure using the fjords-stitching strategy.The synthesis comprised four-fold abnormal m-bromination of four Npivaloylaniline units and Pd_(2)(dba)_(3)/4-Me_(2)NC_(6)H_(4)Pt Bu_(2)-catalyzed intramolecular C-N bond-forming reactions.Subsequent functionalization through Narylations produced a variety of tetraza-embedded octahydrobelt[8]arenes.Further oxidation of p-methoxyphenyl-substituted belt[4]arene[4](1,4-dihydropyridine)with Ag[Al(O^(t)Bu^(F))^(4)]yielded a singlet diradical dication N-doped zigzag belt.

关 键 词：zigzag molecular belt cyclacene arene[4]pyridine meta-bromination of Nacylaniline palladium-catalyzed C-N bond formation diradical dication salt 

分 类 号：O62[理学—有机化学]