Abstract
Reaction of 2- and 3-iodopropenoyltriphenylsilanes with unsaturated tin derivatives affords a mild and general entry to variously functionalized dienoylsilanes. The β-iodo derivative affords, under palladium catalyzed conditions, good yields of the expected compounds, while α-iodo propenoylsilane proved somewhat less reactive under these conditions. The α-iodo derivative could be anyway efficiently reacted with organozinc species to generate several α-branched propenoylsilanes.
Highlights
Since their first discovery by A.G.Brook, acylsilanes[1] have attracted a reasonable deal of attention, due to the striking differences of their reactional behaviour with respect to ordinary carbonyl compounds
Acylsilanes may undergo specific transformations of the -COSiMe3 moiety such as Brook rearrangement,[2] oxidation to carboxylic acids,[3] fluoride promoted
The presence of a double bond together with the acylsilane moiety provides an expansion of acylsilane synthetic potentialities, and opens the way to the possible construction of novel and more versatile synthons
Summary
The reactivity of α- and β-iodo propenoylsilanes: an alternative access to polyunsaturated acylsilanes. Capponi,9, 50121 Firenze, Italy b Dipartimento di Chimica, Università della Basilicata, via N.Sauro, 85, 85100 Potenza, Italy (received Jan 00; accepted Sep 00; published on the web 29 Sep 00)
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