Rhodium(III)-CatalyzedorthoCH Heteroarylation of (Hetero)aromatic Carboxylic Acids: A Rapid and Concise Access to π-Conjugated Poly-heterocycles
| Autor: | Di Wu, Quan Huang, Ruilin Wang, Hu Liu, Qiang Guo, Jingsong You, Xurong Qin, Jingbo Lan, Xiaoyu Li |
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| Rok vydání: | 2015 |
| Předmět: |
Carboxylic Acids
chemistry.chemical_element Stereoisomerism General Chemistry General Medicine Fluorene Conjugated system Combinatorial chemistry Carbon Catalysis Rhodium Electrophilic substitution chemistry.chemical_compound chemistry Heterocyclic Compounds Intramolecular force Organic chemistry Hydrogen |
| Zdroj: | Angewandte Chemie. 127:7273-7276 |
| ISSN: | 0044-8249 |
| DOI: | 10.1002/ange.201501982 |
| Popis: | Rh(III)-catalyzed oxidative C-H/C-H cross-coupling between (hetero)aromatic carboxylic acids and various heteroarenes has been accomplished to construct highly functionalized ortho-carboxy-substituted bi(hetero)aryls. The use of a carboxy group as the directing group obviates tedious steps for installation and removal of extra directing groups, and enables a facile one-step synthesis of ortho-carboxy bi(hetero)aryls. The method provides opportunities for rapid assembly of a library of important fluorene and coumarin-type poly-heterocycles through intramolecular electrophilic substitution or oxidative lactonization. As illustrative examples, the strategy developed herein greatly streamlines accesses to a variety of appealing polyheterocycles such as DTPO (5H-dithieno[3,2-b:2',3'-d]pyran-5-one), CPDTO (cyclopentadithiophen-4-one), and indenothiophenes. |
| Databáze: | OpenAIRE |
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