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
,
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
› Author Affiliations
A part of the work reported in this review and conducted in our lab has been finance by ANR (TRIBAL and AluMeth grants)
Further Information

Publication History

Received: 20 October 2018

Accepted: 29 October 2018

Publication Date:
20 November 2018 (eFirst)

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

 
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