Lead(IV) Acetate

Mihailović, M. Lj.; Čeković, Živorad; Mathes, Brian M.

doi:10.1002/047084289x.rl006

Cited by 1 publication

(1 citation statement)

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“…The vanadium catalyst is not likely to produce the cyclic intermediates as in the case of C–C bond cleavage of 1,2-diols with higher valence inorganic oxidants, such as periodates and lead tetracarboxylates. In the case of lead tetracarboxylate oxidation, cis -glycols react much faster than trans -glycols, whereas cyclic trans -glycols are usually inactive in the case of oxidation by periodates, probably due to difficulty in the formation of cyclic intermediates . It was reported that both cyclic cis - and trans -ditertiary glycols similarly undergo oxidative cleavage in the presence of vanadium oxytrichloride (VOCl 3 ) …”

Section: Resultsmentioning

confidence: 99%

Vanadium-Catalyzed Oxidative C(CO)–C(CO) Bond Cleavage for C–N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides

et al. 2017

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A novel vanadium-catalyzed one-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-diketones to afford N,N'-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic approach to access a variety of imides as well as amides in high yields. Moreover, one-step construction of imide and amide bonds with a long-chain alkyl group is an attractive feature of this protocol.

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Section: Resultsmentioning

confidence: 99%