title: Fe(0)-mediated synthesis of tri- and tetra-substituted olefins from carbonyls: an environmentally friendly alternative to Cr(II).
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 alpha-halo-alpha,beta-unsaturated or alpha,beta-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.
authors.affiliation: Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA. j.falck@utsouthwestern.edu
authors.forename: J R
authors.initials: JR
authors.lastname: Falck
authors.forename: Romain
authors.initials: R
authors.lastname: Bejot
authors.forename: Deb K
authors.initials: DK
authors.lastname: Barma
authors.forename: Anish
authors.initials: A
authors.lastname: Bandyopadhyay
authors.forename: Suju
authors.initials: S
authors.lastname: Joseph
authors.forename: Charles
authors.initials: C
authors.lastname: Mioskowski
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*
chemical_list: D000475:Alkenes