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Oxygen- and Nitrogen-Embedded Zigzag Hydrocarbon Belts |
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| Authors: | Mei-Ling Tan Dr Qing-Hui Guo Dr Xue-Yuan Wang Tan-Hao Shi Dr Qian Zhang Sheng-Kai Hou Prof?Dr Shuo Tong Prof?Dr Jingsong You Prof?Dr Mei-Xiang Wang |
| Institution: | 1. Key Laboratory of Green Chemistry and Technology (MOE), College of Chemistry, Sichuan University, Chengdu, 610064 China;2. Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China |
| Abstract: | 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 resorcin4]arene derivatives through intramolecular SNAr 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 octahydrobelt8]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 octahydrobelt8]arene analogues. |
| Keywords: | nucleophilic aromatic substitution octahydrobelt[8]arenes palladium-catalyzed C?N bond formation strained macrocycles zigzag hydrocarbon belts |