Premium
Rhodium(III)‐Catalyzed ortho CH Heteroarylation of (Hetero)aromatic Carboxylic Acids: A Rapid and Concise Access to π‐Conjugated Poly‐heterocycles
Author(s) -
Qin Xurong,
Li Xiaoyu,
Huang Quan,
Liu Hu,
Wu Di,
Guo Qiang,
Lan Jingbo,
Wang Ruilin,
You Jingsong
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501982
Subject(s) - intramolecular force , chemistry , conjugated system , rhodium , electrophilic aromatic substitution , combinatorial chemistry , catalysis , oxidative coupling of methane , electrophile , stereochemistry , medicinal chemistry , organic chemistry , polymer
Rh III ‐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.