Iron(II) catalyzed reductive radical cyclization reactions of bromoacetals in the presence of NaBH4

optimization studies and mechanistic insights

Sara H. Kyne, Christophe Lévêque, Shiwen Zheng, Louis Fensterbank, Anny Jutand, Cyril Ollivier

Research output: Contribution to journalArticleResearchpeer-review

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7727-7737
Number of pages11
JournalTetrahedron
Volume72
Issue number48
DOIs
Publication statusPublished - 1 Jan 2016
Externally publishedYes

Keywords

  • Electrochemistry
  • Homogenous catalysis
  • Iron
  • NMR spectroscopy
  • Radical cyclization
  • Reduction

Cite this

Kyne, Sara H. ; Lévêque, Christophe ; Zheng, Shiwen ; Fensterbank, Louis ; Jutand, Anny ; Ollivier, Cyril. / Iron(II) catalyzed reductive radical cyclization reactions of bromoacetals in the presence of NaBH4 : optimization studies and mechanistic insights. In: Tetrahedron. 2016 ; Vol. 72, No. 48. pp. 7727-7737.
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Iron(II) catalyzed reductive radical cyclization reactions of bromoacetals in the presence of NaBH4 : optimization studies and mechanistic insights. / Kyne, Sara H.; Lévêque, Christophe; Zheng, Shiwen; Fensterbank, Louis; Jutand, Anny; Ollivier, Cyril.

In: Tetrahedron, Vol. 72, No. 48, 01.01.2016, p. 7727-7737.

Research output: Contribution to journalArticleResearchpeer-review

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