Preparation of 2-trialkylsiloxy-substituted 1,3-dienes and their Diels-Alder/cross-coupling reactions

Department of Chemistry, Wake Forest University, P.O. Box 7486, Winston-Salem, North Carolina 27109, USA.
Organic Letters (Impact Factor: 6.32). 05/2007; 9(9):1623-6. DOI: 10.1021/ol070089e
Source: PubMed

ABSTRACT [reaction: see text] 2-Triethylsiloxy-substituted 1,3-butadiene has been prepared in gram quantities from chloroprene via a simple synthetic procedure. Silatrane and catechol-substituted analogues of this main group element substituted diene were prepared by ligand exchange and characterized by X-ray crystallography in addition to standard spectroscopic techniques. Diels-Alder reactions of these dienes are reported as well as subsequent TBAF assisted/Pd-catalyzed Hiyama cross-coupling reactions of those Diels-Alder adducts.