6798-16-9Relevant academic research and scientific papers
Rhodium(III)-catalyzed ortho c-h heteroarylation of (hetero)aromatic carboxylic acids: A rapid and concise access to π-conjugated poly-heterocycles
Qin, Xurong,Li, Xiaoyu,Huang, Quan,Liu, Hu,Wu, Di,Guo, Qiang,Lan, Jingbo,Wang, Ruilin,You, Jingsong
, p. 7167 - 7170 (2015)
Abstract RhIII-catalyzed oxidative Ci-H/Ci-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. Under construction: The highly regioselective title reaction directly furnishes ortho-carboxy bi(hetero)aryls. The method has the potential to lead to the rapid construction of a library of appealing poly-heterocycles, given the complete regiocontrol, readily available substrates, and functional-group tolerance.
