Jump to main content
Jump to site search


Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes

Author affiliations

Abstract

A simple and efficient iron-catalyzed protodehalogenation of alkyl and aryl halides using phenylhydrosilane is disclosed. The reaction utilizes FeCl3 without the requirement of ligands. Unactivated alkyl and aryl halides were successfully reduced in good yields; sterically hindered tertiary halides were also reduced including the less reactive chlorides. The scalability of this methodology was demonstrated by a gram-scale synthesis with a catalyst loading as low as 0.5 mol%. Notably, disproportionation of phenylsilane leads to diphenylsilane that further reduces the halides. Preliminary mechanistic studies revealed a non-radical pathway and the source of hydrogen is PhSiH3 via deuterium labeling studies. Our methodology represents simplicity and provides a good alternative to typical tin, aluminum and boron hydride reagents.

Graphical abstract: Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes

Back to tab navigation

Supplementary files

Publication details

The article was received on 23 Sep 2018, accepted on 01 Nov 2018 and first published on 02 Nov 2018


Article type: Communication
DOI: 10.1039/C8OB02365D
Citation: Org. Biomol. Chem., 2018, Advance Article
  •   Request permissions

    Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes

    R. Pilli, V. Balakrishnan, R. Chandrasekaran and R. Rasappan, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02365D

Search articles by author

Spotlight

Advertisements