Guest Editor: I. Marek
Beilstein J. Org. Chem. 2013, 9, 234–235. doi:10.3762/bjoc.9.27
Received 24 Jan 2013, Accepted 29 Jan 2013, Published 04 Feb 2013
Following the pioneering Ziegler addition of nucleophiles to nonactivated unsaturated carbon–carbon bonds, the controlled carbometallation reaction has emerged. Since then, reactions that result in the addition of a carbon–metal bond of an organometallic across a carbon–carbon unsaturated system, leading to a new organometallic in which the newly formed carbon–metal bond can be used for further synthetic transformations, are called carbometallation reactions. In the past few decades, the intra- as well as intermolecular additions of various organometallic species to a large variety of alkynes, alkenes and allenes have been successfully reported. Although the carbometallation reaction on alkynes is generally a well-controlled and predictable transformation, leading to large variety of substituted stereocontrolled alkenyl metals, the addition of organometallic species to acyclic nonactivated alkenes still represents a formidable and yet unresolved synthetic challenge. Particularly stimulating would be the regio-, stereo- and enantioselective addition of organometallic species on α,β-disubstituted double bonds, leading to a configurationally stable sp3 organometallic that would subsequently react with electrophiles. This landmark transformation would formally result in the 1,2-bisalkylation of nonactivated alkenes! In this Thematic Series, you will find excellent contributions tackling various problems of carbometallation reactions, indicating a lively and rapidly moving field, and I have no doubt that more elegant transformations of C–C unsaturated bonds will continue to appear, including the enantioselective carbometallation reaction of substituted nonactivated alkenes. I would like to warmly thank all the contributors of this Thematic Series that have beautifully highlighted the state of the art of the field.
I have tremendously enjoyed reading this Thematic Series and I am convinced that you will all share in this pleasure!
Haifa, January 2013