ol070089e_si_003.pdf (3.43 MB)

Preparation of 2-Trialkylsiloxy- Substituted 1,3-Dienes and Their Diels−Alder/Cross-Coupling Reactions

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journal contribution
posted on 26.04.2007 by Ramakrishna R. Pidaparthi, Mark E. Welker, Cynthia S. Day, Marcus W. Wright
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.