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| - Unique Regio- and Stereoselectivity in Pd-CatalyzedChlorocarbonylation Reaction of 2-Phenylethynyl Selenides and2-Alkylethynyl Selenides. Highly Stereoselective Synthesis of2-Seleno-3-chloroacrylates
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| - Regio- and stereoselectivity in the chloropalladation carbonylation reaction of different acetylenicselenides in the presence of 0.05 equiv of PdCl2 and 3 equiv of cupric chloride under 1 atm of carbonmonoxide affording 2-seleno-3-chloroacrylates were investigated. Opposite stereoselectivities wereobserved with 2-phenylethynyl selenides and 2-alkylethynyl selenides: the reactions of 2-phenylethynyl selenides afforded (E)-2-seleno-3-chloro-3-phenylacrylates, while the reactions of 2-alkylethynyl selenides gave (Z)-2-seleno-3-chloro-3-alkylacrylates. A chloropalladation carbonylationmechanism for this reaction was proposed. The regio- and stereoselective chloropalladation of thecarbon−carbon triple bond in acetylenic selenides affords 1-enylpalladium intermediates, in whichthe palladium atom connects with the carbon atom bonding with the selenium atom. Carbonylationin the presence of an alcohol affords 2-seleno-3-chloroacrylates.
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