Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 27, Pages 8470-8475Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b03402
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Funding
- Chinese NSF [81430080, 81373277]
- Major State Basic Research Development Program [2015CB910603]
- Program of Shanghai Subject Chief Scientist [16XD1404600]
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The first example of transition metal-catalyzed meta-selective C-Ar-H nitration of arenes is described. With the use of Ru-3(CO)(12) as the catalyst and Cu(NO3)(2)center dot 3H(2)O 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-C-Ar-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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