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Org Lett. 2000 Jun 01;2(11):1621-4. doi: 10.1021/ol0059100.

Synthesis of periphery-functionalized dendritic molecules using polylithiated dendrimers as starting material.

Organic letters

Wijkens, Jastrzebski, van Der Schaaf PA, Kolly, Hafner, van Koten G

Affiliations

  1. Debye Institute, Department of Metal-Mediated Synthesis, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands, and Ciba Specialty Chemicals, Building K-420, CH-4002 Basel, Switzerland.

PMID: 10841494 DOI: 10.1021/ol0059100

Abstract

A general method for the functionalization of Si-Cl terminated carbosilane dendritic molecules via organolithium or organomagnesium reagents is described. Quantitative exchange of the bromine atoms of 4-bromophenyl-functionalized dendrimers affords polylithiated species that are valuable starting materials for further functionalization, e.g., into pyridyl alcohols. The latter were successfully applied as catalyst precursors in a ruthenium-mediated ring-closure metathesis reaction.

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