Exploiting Poly(ethylene glycol) as a Matrix for Liquid-Phase Organic Synthesis.docVIP

Molecules 2000, 5, 1018-1032 molecules ISSN 1420-3049 ? 2000 by MDPI Exploiting Poly(ethylene glycol) as a Matrix for Liquid-Phase Organic Synthesis Frank Sieber, Paul Wentworth Jr.* and Kim D. Janda* ,1 ,2 Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, CA 92037, U.S.A. 1Tel.: (858)-784 2576, Fax: (858) 784 2590, E-mail: paulw@ 2Tel.: (858)-784 2515, Fax: (858) 784 2595, E-mail: kdjanda@ Received:14February2000;revised form: 31July2000/ Accepted:1August 2000/ Published: 20August 2000 Abstract: Soluble polymer-supported chemistry is a technology that allows the blending of the benefits of polymer-supported synthesis and solution-phase chemistry. Herein, we de- scribe our recent efforts in this area targeted at exploring the scope of poly(ethylene glycol) (PEG) as the matrix. Specifically we describe the use of PEG as a support for triphenyl phos- phine and for the Stille reaction. Keywords: soluble polymer, synthesis, poly(ethylene glycol), triphenyl phosphine, Wittig re- action, Stille reaction. Introduction For many years solid polymers have been dominant both as supports for organic reagents and in combinatorial synthesis [1,2]. However, there are concerns associated with the use of insoluble poly- meric derivatives such as lowered reactivity, site-site interactions, extended reaction times and diffusion- limited reactivity. The use of soluble matrices [3] such as poly(ethylene glycol) [4] circumvents these problems while also allowing for routine monitoring of reaction progress [5,6]. Our efforts in this field have included the development of soluble polymer-supported combinatorial libraries [7], catalysts [8], reagents [9-11], linker strategies [12,13] and synthetic methodology [14,15]. This report details the development and application of a poly(ethylene glyco