- Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds
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Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.
- Yang, Tonghao,Lin, Yajun,Yang, Chaoqun,Yu, Wei
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supporting information
p. 6097 - 6102
(2019/11/20)
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- ON THE FACILE DEHYDROHALOGENATION OF AMINO ACID DERIVED CHLOROMETHYL KETONES.
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Amino acid derived chloromethyl ketones are shown to undergo a general dehydrohalogenation reaction under mild, basic, nonnucleophilic conditions to afford α-β-unsaturated ketones.
- Gordon, E. M.,Pluscec, Jelka,Delaney, N. G.,Natarajan, S.,Sundeen, J.
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p. 3277 - 3280
(2007/10/02)
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