Consequences of Affinity in Heterogeneous Catalytic Reactions:  Highly Chemoselective Hydrogenolysis of Iodoarenes

The catalytic hydrodeiodination reaction using molecular hydrogen and Pd/C has been revisited. It is shown, for the first time, that the chemoselectivity of this reaction is controlled by the high affinity of the iodinated compound for the catalyst. This reaction is compatible with most easily reduc...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 65; no. 21; pp. 7183 - 7186
Main Authors Ambroise, Yves, Mioskowski, Charles, Djéga-Mariadassou, Gérald, Rousseau, Bernard
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.10.2000
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENT
HIGH SPECIFIC RADIOACTIVITY
ANALOG
RADIOLIGAND
MEMBRANE
AFLATOXIN-B2
PHOSPHOLIPIDIC PROBE
RECEPTORS
PROTEINS
SELECTIVITY
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Summary:The catalytic hydrodeiodination reaction using molecular hydrogen and Pd/C has been revisited. It is shown, for the first time, that the chemoselectivity of this reaction is controlled by the high affinity of the iodinated compound for the catalyst. This reaction is compatible with most easily reducible functional groups (nitro, aldehyde, olefin, etc.). Using this reaction, the first general method for tritium labeling of 3-(trifluoromethyl)-3-phenyldiazirine is described.
Bibliography:istex:D196EC167BA5314F244128CE136939FA7507F549
ark:/67375/TPS-7NMVPN2G-2
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0012243