TY - JOUR
T1 - Fe(0)-mediated synthesis of tri- and tetra-substituted olefins from carbonyls
T2 - An environmentally friendly alternative to Cr(II)
AU - Falck, J R
AU - Bejot, Romain
AU - Barma, Deb K.
AU - Bandyopadhyay, Anish
AU - Joseph, Suju
AU - Mioskowski, Charles
PY - 2006/10/13
Y1 - 2006/10/13
N2 - 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.
AB - 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.
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U2 - 10.1021/jo061445u
DO - 10.1021/jo061445u
M3 - Article
C2 - 17025309
AN - SCOPUS:33750000015
SN - 0022-3263
VL - 71
SP - 8178
EP - 8182
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -