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Synthesis 2016; 48(04): 520-534
DOI: 10.1055/s-0035-1560380
DOI: 10.1055/s-0035-1560380
paper
Regioselective Allylation of Carbon Electrophiles with Alkenylsilanes under Dual Catalysis by Cationic Platinum(II) Species
Weitere Informationen
Publikationsverlauf
Received: 12. Oktober 2015
Accepted after revision: 05. November 2015
Publikationsdatum:
16. Dezember 2015 (online)
Abstract
In the presence of catalytic amounts of platinum(II) chloride and silver(I) hexafluoroantimonate, (Z)-alkenylsilanes reacted with various carbon electrophiles (acetals, aminals, carboxylic anhydrides, alkyl chlorides, etc.) at the γ-position to give allylation products. A plausible mechanism for the platinum-catalyzed allylation involves alkene migration of alkenylsilanes to allylsilanes and subsequent allylation of carbon electrophiles, both of which are catalyzed by a cationic platinum(II) species.
Key words
acetals - alkenylsilanes - allylation - allylsilanes - tandem reaction - platinum catalysisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560380.
- Supporting Information
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Other recent studies:
Isomerization of alkenylsilanes to allylsilanes:
Pt(II)-catalyzed alkene migration:
Recent studies:
Synthesis of aminals 6:
Tandem Pt(II) catalysis: