Monomeric Octahedral Ruthenium(II) Complex Enabled meta-C-H Nitration of Arenes with Removable Auxiliaries
A removable oxime-assisted meta-C-H nitration of arenes is reported. Mechanistic investigations and DFT calculations reveal a new monomeric octahedral ruthenium(II) complex is responsible for the meta-selective nitration. Dioxygen as a cooxidant is crucial for achieving high conversion and good yields. Moreover, the utility of the present reaction protocol is further showcased by the late-stage modification of the clinical CNS drugs Diazepam and Fluvoxamine.
Fan, Zhoulong,Li, Jie,Lu, Heng,Wang, Dong-Yu,Wang, Chao,Uchiyama, Masanobu,Zhang, Ao
supporting information
p. 3199 - 3202
(2017/06/23)
Selective ortho -bromination of substituted benzaldoximes using Pd-catalyzed C-H activation: Application to the synthesis of substituted 2-bromobenzaldehydes
Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.
Oxidative conversion of aldoximes into carboxylic acid esters
Aromatic and aliphatic aldoximes or their O-methyl ethers can be efficiently converted into the corresponding carboxylic acid esters by treatment with an alcoholic solution of 30% hydrogen peroxide in the presence of catalytic amounts of 2-nitrobenzeneseleninic acid. Primary alcohols give excellent to good yields, secondary ones - good to moderate, but with tertiary alcohols no esterification is observed.
Said,Skarzewski,Mlochowski
p. 1851 - 1862
(2007/10/02)
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