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Application of the Silylative Coupling Reaction in Organic Synthesis

Piotr Pawluć ,  Bogdan Marciniec 

Adam Mickiewicz University, Faculty of Chemistry, Grunwaldzka 6, Poznań 60-780, Poland

Abstract

The catalytic silylative coupling reaction of olefins with vinylsilanes allows selective synthesis of stereochemically defined unsaturated organosilicon compounds from commercially available substrates [1]. The products can be further used in stereoselective organic synthesis and the methods of their synthesis can help develop of the original synthetic strategies using the designed and defined organosilicon monomers as intermediates in the synthesis of desired organic products by sequential or tandem process [2].

Intensive study of sequential silylative coupling – desilylation reactions (catalytic Hiyama coupling acylation, halodesilylation) resulted in the development of original methods of synthesis of a series of di- or trisubstituted alkenes such as alkenyl halides, styryl ketones, stilbenes, styrylcarbazoles, styryl alkyl ethers and other systems containing π-conjugated double bonds [3].

[1] B. Marciniec, Acc. Chem. Res. 2007, 40, 943

[2] P. Pawluć, W.  Prukała, B. Marciniec,  Eur. J. Org. Chem. 2010, 219.

[3] (a) P. Pawluć, J. Szudkowska, G. Hreczycho, B. Marciniec, J. Org. Chem., 2011, 76, 6438; (b) P. Pawluć, A. Franczyk, J. Walkowiak, G. Hreczycho, M. Kubicki, B. Marciniec, Org. Lett., 2011, 13, 1976; (c) P. Pawluć, G. Hreczycho, J. Szudkowska, M. Kubicki, B. Marciniec, Org. Lett. 2009, 11, 3390; (d) P. Pawluć, G. Hreczycho, A. Suchecki, M. Kubicki, B. Marciniec, Tetrahedron 2009, 65, 5497; (e) P. Pawluć, G. Hreczycho, J. Walkowiak, B. Marciniec, Synlett 2007, 13, 2061.

 

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Presentation: Invited oral at VIII Multidyscyplinarna Konferencja Nauki o Leku, by Piotr Pawluć
See On-line Journal of VIII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2012-03-01 13:26
Revised:   2012-04-13 14:44