Reversible Substrate Anchoring in Solid-Supported Organic Synthesis
A. Porzelle, W.-D. Fessner*
Technische Universität Darmstadt, Germany
21 September 2005 (online)
The authors have proposed noncovalent solid-phase organic synthesis (NC-SPOS) as a novel concept for facilitated organic processes and have demonstrated that several synthetic reactions such as Barbier reaction, [3+2] cycloaddition, and Pd-catalyzed C-C cross-coupling reactions (Heck and Sonogashira reactions) can be carried out under such conditions. For example, when C18-modified reversed-phase silica gel and an N-alkylated acridon derivative were used as the hydrophobic matrix as well as the hydrophobic anchor moiety, homoallyl alcohol 3 was obtained in 90% yield from the reaction of allyl bromide with compound 2.