Synthesis 2016; 48(24): 4400-4422
DOI: 10.1055/s-0036-1588877
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Developments in the Chemistry of Vinylsiloxanes

Kiran Indukuri
Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST), Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium   Email: olivier.riant@uclouvain.be
,
Loïc Cornelissen
Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST), Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium   Email: olivier.riant@uclouvain.be
,
Olivier Riant*
Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST), Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium   Email: olivier.riant@uclouvain.be
› Author Affiliations
Further Information

Publication History

Received: 22 July 2016

Accepted: 26 July 2016

Publication Date:
15 September 2016 (online)


Abstract

Vinylsiloxanes are vital systems in modern organic chemistry and are widely utilized as vinylic precursors in cross-coupling reactions. The ease of regio- and stereoselective synthesis of vinylsiloxanes led to the rapid development of highly selective vinyl analogues in organic synthesis. This review describes different routes for the synthesis of vinylsiloxanes and highlights their recent developments in various metal-catalyzed cross-coupling reactions for the formation of new carbon–carbon and carbon–heteroatom bonds. It also covers some applications of vinylsiloxanes in natural product synthesis and in carbon–oxygen bond formation via Tamao–Fleming oxidation. The mechanisms of the selected reactions are discussed alongside.

1 Introduction

2 Synthesis of Vinylsiloxanes

3 Reactions of Vinylsiloxanes

3.1 Palladium-Catalyzed Reactions

3.2 Copper-Catalyzed Reactions

3.3 Ir-, Ru-, Co-, and Ni-Catalyzed Reactions

3.4 Vinylation of Carbonyl Compounds

3.5 Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

3.6 Cycloaddition Reactions

3.7 Radical Reactions

3.8 Tamao–Fleming Oxidation of Vinylsiloxanes

3.9 Miscellaneous Reactions

4 Summary and Conclusions

 
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