Synthesis and Reactivity of Mixed Dimethylalkynylaluminum Reagents

Riccardo Piccardi; Serge Turcaud; Erica Benedetti; Laurent Micouin

doi:10.1055/s-0037-1610392

Synthesis, Inhaltsverzeichnis

CC BY ND NC 4.0 · Synthesis 2019; 51(01): 97-106
DOI: 10.1055/s-0037-1610392

short review

Copyright with the author

Synthesis and Reactivity of Mixed Dimethylalkynylaluminum Reagents

Riccardo Piccardi

,

Serge Turcaud

,

Erica Benedetti

,

Laurent Micouin *

Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR 8601 CNRS-Université Paris Descartes, Faculté des Sciences Fondamentales et Biomédicales, 45 rue des Saints-Pères, 75006 Paris, France eMail: Laurent.micouin@parisdescartes.fr

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Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Organoaluminum derivatives are mostly appreciated for their Lewis acidity properties, but generally not considered as reagents of choice in synthetic transformations involving the creation of C–C bonds. Among these species, dimethylalkynylaluminum reagents represent a special class of compounds, with, in many cases, unique reactivity. This review summarizes the preparation and reactivity of these organometallic reagents with a focus on their synthetic potential.

1 Introduction

2 Preparation of Dimethylalkynylaluminum Reagents

3 Reactivity of Dimethylalkynylaluminum Reagents

3.1 Reactions with Csp³ Electrophiles

3.2 Reactions with Csp² Electrophiles

4 Transition-Metal-Catalyzed Reactions

4.1 Addition to α,β-Unsaturated Enones

4.2 Coupling Reactions

5 Triple Bond Reactivity

6 Conclusion

Key words

organometallics - alkynes - organoaluminum reagents - alkynylation - metalation

Volltext

Referenzen

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