Fe(0)-mediated synthesis of tri- and tetra-substituted olefins from carbonyls: An environmentally friendly alternative to Cr(II)

J R Falck, Romain Bejot, Deb K. Barma, Anish Bandyopadhyay, Suju Joseph, Charles Mioskowski

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

Fe(0) was investigated as a cost-effective, environmentally friendly alternative to Cr(II) for the olefination of carbonyls by activated polyhalides. In many instances, Fe(0) was equivalent or superior to Cr(II). Notably, Fe(0), but not Cr(II), proved compatible with a wide range of functionality, inter alia, unprotected phenol, aryl nitro, carboxylic acid, and alkyl nitrile. A surprising reversal of stereoselectivity for aldehydes versus ketones was observed using both metals. The resultant α-halo-α,β- unsaturated or α,β-unsaturated carboxylic acids, esters, and nitriles are common structural elements in numerous compounds of interest as well as key intermediates in the preparation of other functionality.

Original languageEnglish (US)
Pages (from-to)8178-8182
Number of pages5
JournalJournal of Organic Chemistry
Volume71
Issue number21
DOIs
Publication statusPublished - Oct 13 2006

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this