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Synlett 2013; 24(17): 2199-2215
DOI: 10.1055/s-0033-1339842
DOI: 10.1055/s-0033-1339842
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Highly Selective Addition of Phosphorus-Containing Interelement Compounds to Alkynes
Weitere Informationen
Publikationsverlauf
Received: 19. Juli 2013
Accepted after revision: 22. August 2013
Publikationsdatum:
07. Oktober 2013 (online)
Abstract
A series of addition reactions of phosphorus-containing ‘interelement’ compounds (bearing a heteroatom–heteroatom single bond) with alkynes have been found to take place under different conditions. Transition-metal-catalyzed reactions of diphosphines with alkynes in the presence of hydrosilanes and a small amount of oxygen afford hydrophosphinylation products regioselectively. Under radical conditions, diphosphines add to alkynes to afford the corresponding bis-phosphination products. Furthermore, a combination of diphosphines and dichalcogenides results in a series of chalcogenophosphination steps leading to 1,2-disubstituted alkenes from alkynes. In addition, the reaction of an alkyne with a diphosphine and iodine selectively proceeds via an ionic mechanism to give the corresponding vinyl iodide. These addition reactions may provide powerful tools for the synthesis of a variety of heteroatomic compounds with excellent regio- and/or stereoselectivity.
1 Introduction
2 Transition-Metal-Catalyzed Addition Reactions
2.1 Transition-Metal-Catalyzed Reactions of Diphosphines
2.2 Transition-Metal-Catalyzed Reactions of Interelement Compounds Bearing Phosphorus–Heteroatom Bonds
3 Radical Addition Reactions
3.1 Radical Addition Reactions of Diphosphines
3.2 Radical Addition Reactions of Interelement Compounds Bearing Phosphorus–Heteroatom Bonds
4 Ionic Addition Reactions of Interelement Compounds Bearing Phosphorus–Heteroatom Bonds
5 Conclusion
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For the photoinduced thioselenation of other carbon-carbon unsaturated bonds, see:
Other addition reactions of alkynes involving the simultaneous introduction of thio and phosphorus groups were reported, see:
For both aluminum- and phosphorus-substituted alkenes, for example, see: