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Solid-Phase Organic Synthesis and Catalysis: Some Recent Strategies Using Alumina, Silica, and Polyionic Resins

DOI: 10.1155/2013/614829

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Abstract:

Solid-phase organic synthesis (SPOS) and catalysis have gained impetus after the seminal discovery of Merrifield’s solid-phase peptide synthesis and also because of wide applicability in combinatorial and high throughput chemistry. A large number of organic, inorganic, or organic-inorganic hybrid materials have been employed as polymeric solid supports to promote or catalyze various organic reactions. This review article provides a concise account on our approaches involving the use of (i) alumina or silica, either having doped with metal salts or directly, and (ii) polyionic resins to either promote various organic reactions or to immobilize reagents/metal catalysts for subsequent use in hydrogenation and cross-coupling reactions. The reaction parameters, scopes, and limitations, particularly in the context of green chemistry, have been highlighted with pertinent approaches by other groups. 1. Introduction The concept of solid-phase organic synthesis (SPOS) dates back mid-1940s, and the solid-phase peptide synthesis in 1960s developed by Merrifield has been a pioneering work [1]. Over the last two decades, there has been a surge generating tremendous interest in expanding this field of solid-phase synthesis [2–10]. There is a clear emphasis in synthetic chemistry towards developing environmentally friendly and sustainable routes to a myriad of materials. The emphasis is most apparent in the growth of green chemistry [11–14]. According to Paul Anastas—one of the founders of the concepts of green chemistry, “Catalysis is a foundational stone of Green Chemistry” [11, 12]. One important aspect of clean technology is the usage of environmentally friendly surface catalysts, typically a solid catalyst that can be easily recovered when the reaction is complete [15]. Polymer supports play a critical role in combinatorial chemistry, and consequently, solid-phase organic synthesis continues to grow in importance [16–23]. One of the major advantages of this technique that has attracted attention of the chemists is the clean isolation of the products by simple filtration. As a result, this technique has become a valuable tool in combinatorial chemistry and high throughput chemistry, an integral part of drug discovery and research [24–26]. The solid-phase organic synthesis of small organic molecules depends largely on the adaptation of solution reactions to solid phase [27]. Alternative synthetic routes that avoid need of any toxic solvents and reduce the number of steps with high atom economy and energy efficiency are some of the key features of green chemistry. On

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