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- Title
Rhodium(III)-Catalyzed ortho CH Heteroarylation of (Hetero)aromatic Carboxylic Acids: A Rapid and Concise Access to π-Conjugated Poly-heterocycles.
- Authors
Qin, Xurong; Li, Xiaoyu; Huang, Quan; Liu, Hu; Wu, Di; Guo, Qiang; Lan, Jingbo; Wang, Ruilin; You, Jingsong
- Abstract
RhIII-catalyzed oxidative CH/CH 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 (5 H-dithieno[3,2- b:2′,3′- d]pyran-5-one), CPDTO (cyclopentadithiophen-4-one), and indenothiophenes.
- Subjects
RHODIUM catalysts; CARBON-hydrogen bonds; CARBOXYLIC acids; HETEROCYCLIC compounds; COUMARINS; ELECTROPHILIC substitution reactions
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 24, p7167
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201501982