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Silylcarbonylation of styrenes catalyzed by iridium(I) siloxide complexes

Paper ID Volume ID Publish Year Pages File Format Full-Text
41528 45892 2010 8 PDF Available
Title
Silylcarbonylation of styrenes catalyzed by iridium(I) siloxide complexes
Abstract

This paper reports the study of iridium(I) catalyzed the incorporation of HSiMe2Ph and carbon monoxide to styrene and its derivatives. Comparative catalytic tests performed for the various iridium(I) precursors [{Ir(μ-X)(diene)}2] (where X = OMe, OAc, OSiMe3; diene = 1,5-cyclooctadiene (cod), tetrafluorobenzobarrelene (tfb)) and [Ir(CO)3(PCy3)(SiPh3)] showed that the binuclear complex [{Ir(μ-OSiMe3)(cod)}2] is the most efficient catalyst of the process studied and gives the main silylcarbonylation product, i.e. enol silyl ethers of acylsilanes (RCH2CHC(OSiMe2Ph)SiMe2Ph, where R = Ph, aryl) with relatively good yield. It enabled us to synthesize and isolate the exemplary acylsilane silyl enolates illustrating the potential application of binuclear siloxide iridium(I) complex in the synthesis of so useful in organic synthesis unsaturated organosilicon derivatives. Catalytic results as well as the detailed study of stoichiometric reaction of [{Ir(μ-OSiMe3)(cod)}2] and [Ir(CO)2(PCy3)(OSiMe3)] with the reaction substrates also under pressure of CO enabled us to propose a general catalytic scheme of the silylcarbonylation process including the formation of enol silyl ethers of acylsilanes as a main product accompanied by silyl enol ethers of aldehydes and products of styrene hydrosilylation.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (53 K)Download as PowerPoint slideResearch highlights▶ Application of iridium(I) siloxide complexes for catalytic silylcarbonylation of olefins. ▶ [{Ir(μ-OSiMe3)(cod)}2] effectively catalyzes formation of acylsilane silyl enolates. ▶ Exemplary syntheses of acylsilane derivatives are presented. ▶ Scheme of catalysis of styrene silylcarbonylation by [{Ir(μ-OSiMe3)(cod)}2] is also presented.

Keywords
Silylcarbonylation; Iridium(I) siloxide complexes; Enol silyl ethers of acylsilanes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 390, Issues 1–2, 20 December 2010, Pages 94–101
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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Full-text PDF Download
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