期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 71, 期 21, 页码 8178-8182出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo061445u
关键词
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资金
- NIDDK NIH HHS [P01 DK038226, P01 DK038226-220006, DK38226] Funding Source: Medline
- NIGMS NIH HHS [GM31278, R01 GM031278-24, R01 GM031278] Funding Source: Medline
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.
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