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We report herein the synthesis of diverse O\/N\u2010doped zigzag hydrocarbon belts based on selective bridging of the fjords of resorcin[4]arene derivatives through intramolecular S<jats:sub>N<\/jats:sub>Ar and palladium\u2010catalyzed intermolecular C\u2212N bond formation reactions. Preorganized conformations of mono\u2010macrocyclic, half\u2010belt and quasi\u2010belt compounds were revealed to facilitate cyclization reactions to construct heteroatom\u2010linked octahydrobelt[8]arenes. The acquired products had strained square\u2010prism\u2010shaped belt structures in which all six\u2010membered heterocyclic rings adopted an unusual boat conformation with equatorially configured alkyl groups. The unprecedented heteroatom\u2010bearing belts also exhibited different photophysical and redox properties to those of octahydrobelt[8]arene analogues.<\/jats:p>","DOI":"10.1002\/anie.202013149","type":"journal-article","created":{"date-parts":[[2020,10,13]],"date-time":"2020-10-13T02:25:48Z","timestamp":1602555948000},"page":"23649-23658","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":50,"title":["Oxygen\u2010 and Nitrogen\u2010Embedded Zigzag Hydrocarbon Belts"],"prefix":"10.1002","volume":"59","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7983-3432","authenticated-orcid":false,"given":"Mei\u2010Ling","family":"Tan","sequence":"first","affiliation":[{"name":"Key Laboratory of Green Chemistry and Technology (MOE) College of Chemistry Sichuan University  Chengdu 610064 China"},{"name":"Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE) Department of Chemistry Tsinghua University  Beijing 100084 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