期刊
ORGANIC LETTERS
卷 20, 期 6, 页码 1517-1520出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00223
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资金
- Polish National Science Centre [MAESTRO 2012/06/A/ST5/00216, PRELUDIUM 2015/19/N/ST5/00826]
- Global Research Laboratory Program [2014K1A1A2064569]
- Foundation for Polish Science
Tetraarylpyrrolo[3,2-b]pyrroles (TAPPs) possessing [1,1'-biphenyl]-2-yl substituents attached to the pyrrolic nitrogen atoms undergo selective double dehydrogenative cyclization accompanied by twofold 1,2-aryl migration under oxidative aromatic coupling conditions. The structure of the product of the rearrangement has been unambiguously confirmed by X-ray crystallography, and the reaction pathway is supported by density functional theory (DFT) calculations. Six-membered ring formation (requiring rearrangement of aryl substituents around the core) is energetically preferred over seven-membered ring closure, and a 1,2-aryl shift occurs via arenium cation intermediate.
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