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Oxygen‐ and Nitrogen‐Embedded Zigzag Hydrocarbon Belts
Author(s) -
Tan MeiLing,
Guo QingHui,
Wang XueYuan,
Shi TanHao,
Zhang Qian,
Hou ShengKai,
Tong Shuo,
You Jingsong,
Wang MeiXiang
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202013149
Subject(s) - heteroatom , chemistry , intramolecular force , zigzag , intermolecular force , aromaticity , hydrocarbon , alkyl , palladium , stereochemistry , molecule , catalysis , organic chemistry , geometry , mathematics
Despite the aesthetically appealing structures and tantalizing physical and chemical properties, zigzag hydrocarbon belts and their heteroatom‐embedded analogues remain challenging synthetic targets. We report herein the synthesis of diverse O/N‐doped zigzag hydrocarbon belts based on selective bridging of the fjords of resorcin[4]arene derivatives through intramolecular S N Ar and palladium‐catalyzed intermolecular C−N bond formation reactions. Preorganized conformations of mono‐macrocyclic, half‐belt and quasi‐belt compounds were revealed to facilitate cyclization reactions to construct heteroatom‐linked octahydrobelt[8]arenes. The acquired products had strained square‐prism‐shaped belt structures in which all six‐membered heterocyclic rings adopted an unusual boat conformation with equatorially configured alkyl groups. The unprecedented heteroatom‐bearing belts also exhibited different photophysical and redox properties to those of octahydrobelt[8]arene analogues.