Chelation Assistance in the Activation of C-S and C-O Bonds
Resource
Synlett 1996: 201-208
Journal
Synlett
Journal Volume
1996
Journal Issue
3
Pages
201-208
Date Issued
1996
Author(s)
Luh, T.-Y.
Abstract
A chelation approach to activate C-S and C-O bonds is described. In the area of organosulfur chemistry, the theme is based on the formation of a chelation complex which results in the enhancement of the reactivity of the aliphatic carbon-sulfur bonds in the nickel-catalyzed cross coupling reactions with the Grignard reagent. Various neighboring heteroatom substituents (OR, OH, NR2, SR as well as another dithioacetal group) can facilitate the olefination of a dithioacetal group. Depending on the relative position of the newly formed double bond and the remaining dithioacetal moiety, tandem olefinations of bisdithioacetals occur to yield the corresponding dienes under these conditions. Polythioethers afford the corresponding degradation products via β-sulfur elimination process. 1,3-Dimercapto- and 1,3-dithiolatopropanes undergo desulfurative cyclopropanation under these reaction conditions. The reactions of dihydrothiapyrans with MeMgI in the presence of the nickel catalyst proceeds smoothly to give vinyl cyclopropanes.
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journal article
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