Published in
Elsevier, Tetrahedron, 48(72), p. 7727-7737, 2016
DOI: 10.1016/j.tet.2016.08.039
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Iron(II) catalyzed reductive radical cyclization reactions of bromoacetals in the presence of NaBH4: optimization studies and mechanistic insights
,
Christophe Lévêque,
Shiwen Zheng,
Louis Fensterbank,
Anny Jutand,
Cyril Ollivier
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Abstract
Abstract 5-Exo-trig radical reductive cyclization reactions of bromoacetals are catalyzed by iron in the presence of the reducing agent NaBH4. Both iron(II) and iron(III) were found to effectively mediate these reactions. As shown by cyclic voltammetry, iron(III) can be reduced to an iron(II) precatalyst before passing through an identical reaction mechanism in which monoelectronic activation of the substrate would occur by an anionic hydridoiron(I) complex. Further studies have established that both the substrate (iodo- vs bromo-derivative) and the precatalytic mixture are decisive in determining the reaction outcome.