Rhodium(III)‐Catalyzed ortho CH Heteroarylation of (Hetero)aromatic Carboxylic Acids: A Rapid and Concise Access to π‐Conjugated Poly‐heterocycles1. Issue 24 (27th April 2015)

• Record Type: Journal Article
• Authors: Qin, Xurong; Li, Xiaoyu; Huang, Quan; Liu, Hu; Wu, Di; Guo, Qiang; Lan, Jingbo; Wang, Ruilin; You, Jingsong
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 24(2015)
• Page Start: 7167
• Page End: 7170
• Publication Date: 2015-04-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201501982
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>ortho</italic>‐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 <italic>ortho</italic>‐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<italic>H</italic>‐dithieno[3, 2‐<italic>b</italic>:2′, 3′‐<italic>d</italic>]pyran‐5‐one), CPDTO (cyclopentadithiophen‐4‐one), and indenothiophenes.</p> </abstract>