† CAS Key Laboratory of Receptor Research, and Synthetic Organic &
Medicinal Chemistry Laboratory (SOMCL), Shanghai Institute of Materia
Medica (SIMM), Chinese Academy of Sciences, Shanghai 201203, China
Medicinal Chemistry Laboratory (SOMCL), Shanghai Institute of Materia
Medica (SIMM), Chinese Academy of Sciences, Shanghai 201203, China
‡ University of Chinese Academy of Sciences, Beijing 100049, China
J. Am. Chem. Soc., Article ASAP
DOI: 10.1021/jacs.6b03402
Publication Date (Web): May 15, 2016
Copyright © 2016 American Chemical Society
Abstract
The first example of transition metal-catalyzed meta-selective CAr–H nitration of arenes is described. With the use of Ru3(CO)12 as the catalyst and Cu(NO3)2·3H2O as the nitro source, a wide spectrum of arenes bearing diversified N-heterocycles
or oximido as the directing groups were nitrated with meta-selectivity
exclusively. Mechanism studies have demonstrated the formation of a new
18e-octahedral ruthenium species as a key ortho-CAr–H metalated intermediate, which may be responsible for the subsequent meta-selective electrophilic aromatic substitution (SEAr).
Moreover, this approach provides a fast-track strategy for atom/step
economical synthesis of many useful pharmaceutical molecules.
or oximido as the directing groups were nitrated with meta-selectivity
exclusively. Mechanism studies have demonstrated the formation of a new
18e-octahedral ruthenium species as a key ortho-CAr–H metalated intermediate, which may be responsible for the subsequent meta-selective electrophilic aromatic substitution (SEAr).
Moreover, this approach provides a fast-track strategy for atom/step
economical synthesis of many useful pharmaceutical molecules.
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