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Organic Synthesis Using Clay and Clay-Supported Catalysts.Pdf Applied Clay Science 53 (2011) 106–138 Contents lists available at ScienceDirect Applied Clay Science journal homepage: www.elsevier.com/locate/clay Review Article Organic synthesis using clay and clay-supported catalysts Gopalpur Nagendrappa ⁎,1 Department of Chemistry, Bangalore University, Bangalore 560 001, India article info abstract Article history: Clays and modified clays are used to catalyze various types of organic reactions such as addition, Michael Received 20 May 2010 addition, carbene addition and insertion, hydrogenation, allylation, alkylation, acylation, pericyclic reactions, Received in revised form 17 October 2010 condensation reactions, aldol formation, imine synthesis, diazotization reactions, synthesis of heterocycles, Accepted 19 October 2010 esterification reactions, rearrangement/isomerization reactions, cyclization reactions, oxidation of alcohols, Available online 6 October 2010 dehydrogenation, epoxidation and several more. Clays function as Brønsted and/or Lewis acids, or as bases. Clays with combined acidic and basic properties have been developed by simple procedures of modification. Keywords: Clay mineral Such clays are employed to catalyze a sequence of acid and base-catalyzed reactions in one pot. Good Activated bentonite enantioselectivity and stereoselectivity are achieved using chiral organic compounds and chiral complexes Montmorillonite intercalated between clay layers. Examples from recent literature are described here. Saponite © 2010 Elsevier B.V. All rights reserved. Organic synthesis Heterogeneous catalyst 1. Introduction compatibility and cheapness, much effort is expended in discovering newer methods of using clays in their native and modified forms as Clays are widespread, easily available and low-cost chemical catalysts for diverse organic reactions. substances. Both in their native state and in numerous modified Clays have a long history of use as catalysts and as supports in organic forms, clays are versatile materials that catalyze a variety of chemical reactions (Vogels et al., 2005). Several excellent reviews on clay reactions. Just as they can be molded into any shape, their micro catalyzed organic reactions have appeared in the recent past (Varma, structure can be changed to suit chemists' needs to promote diverse 2002; Dasgupta and Török, 2008; Ranu and Chattopadhyay, 2009). Zhou chemical reactions. It is convincingly argued that clays initiated, (2010) has briefly summarized the emerging trends in synthetic clay- supported and sustained the process of formation of small molecules based materials. The present review attempts to report some of the on the earth millions of years ago, which gradually developed into developments that have taken place in the area of organic synthesis more complex molecules. In the course of time, there emerged from using clays and clay-supported catalysts during the past decade. the latter the self replicating assemblies that evolved into simple life Much of the work on clays focus on the use of “normal” smectites, forms and progressed to the present elaborate living world of plants mostly the commercially available K10 and KSF or native varieties with and animals (Saladino et al., 2004; Stern and Jedrzejas, 2008; Ciciriello Brønsted or Lewis acid sites and enhancing their catalytic performance et al., 2009). by pillaring techniques to manipulate the pore size, surface area and Clays are nanoparticles with layered structures. The layers possess stability or replace interlayer cations to alter acid-base properties (Singh net negative charge that is neutralized by cations such as Na+,K+,Ca2+, et al., 2007; Moronta et al., 2008). Clays have been intercalated with a etc., which occupy the interlamellar space. The amazing amenability of variety of inorganic and organic ions, metal complexes, and organic clays for modification lies in the fact that these interlamellar cations can compounds. These have brought about radical changes in the be very easily replaced by other cations or other molecules. Molecules performance of clays in terms of increasing the rates of reactions, yields, can be covalently anchored to layer atoms. All this can be done by very product selectivity, and stereoselectivity including enantioselectivity. simple procedures. This provides tremendous scope for altering the Clays have been modified to act as acid-base combination catalysts properties of clays like acidity, pore size, surface area, polarity and other which have been employed to carry out acid and base-catalyzed characteristics that govern their performance as catalysts. Because of reactions in a sequence in one pot (Motokura et al., 2005, 2009). The these wide ranging possibilities, in addition to their environmental possibilities seem to be limited only to the power of our imagination to modify clays for any reaction. The review describes seven types of organic reactions in as many ⁎ Permanent address: #13, Basappa Layout, Gavipuram Extension, Bangalore-560019, sections—Addition reactions, Condensation reactions, Diels–Alder and India. Tel.: +91 80 26670899. fi – E-mail address: [email protected]. related reactions, Esteri cation reactions, Friedel Crafts and related 1 Retired from the organization. reactions, Isomerization reactions, and Oxidation reactions. It should be 0169-1317/$ – see front matter © 2010 Elsevier B.V. All rights reserved. doi:10.1016/j.clay.2010.09.016 G. Nagendrappa / Applied Clay Science 53 (2011) 106–138 107 Scheme 1. Addition of allylsilanes to aromatic and aliphatic alkenes. noted that the literature covered is essentially from articles in interlamellar space of the catalyst and is helped by its Lewis acid mainstream journals published between 2000 and 2010, with a few character. This modified Hosomi–Sakurai reaction is environment exceptions; the patent literature is completely omitted. As a result the friendly and delivers protected homoallylic ethers due to six membered review is not exhaustive; some aspects and several types of reactions are pericyclic transition state of ene reaction (Scheme 3). left out for various reasons. The reaction with aliphatic aldehydes and ketones was successful in some cases, which are given below, with yields of the homoallylic 2. Addition reactions ether products mentioned in the parentheses. In this section examples of addition reactions leading to carbon– CHO O O carbon and carbon–heteroatom bonds are considered. In the past ten CHO years several groups of workers have reported a variety of addition CHO CHO reactions efficiently facilitated by montmorillonite clays. They include (70%) (90%) (47%) (61%) (16%) (25%) addition of allylsilanes to C=C and C=O bonds, carbene addition, epoxidation, Michael addition, etc. Some of them are considered here. Motokura et al. (2010) have found excellent catalytic performance by proton-exchanged montmorillonite in the addition of allylsilanes Allylation of ketones and aldehydes has been carried out using to aromatic and aliphatic alkenes (Scheme 1). potassium salts of allyl- and crotyltrifluoroborates using borontrifluoride The mechanism has been studied in detail, a summary of which is etherate or montmorillonite K10 catalyst (Nowrouzi et al., 2009) presented in Scheme 2. (Scheme 4). The authors find that K10 clay catalyzed reactions are robust, Activated montmorillonite K10 clay was found to catalyze the straightforward and easy to work up, and scalable, which means the K10 reaction of allyl trimethylsilane with aromatic aldehydes to give catalyzed reaction is far superior to the Lewis acid-catalyzed one. homoallylic silyl ethers (Dintzner et al., 2009). The authors suggest Other supports like alumina, silica gel and charcoal proved to be inferior. that the reaction proceeds through a cyclic transition state in the The yields are generally excellent. In each case one stereoisomer is Scheme 2. Mechanism of addition of allylsilanes to aromatic and aliphatic alkenes. Scheme 3. Reaction of allyl trimethylsilane with aromatic aldehydes. 108 G. Nagendrappa / Applied Clay Science 53 (2011) 106–138 Scheme 4. Allylation of ketones and aldehydes using potassium salts of allyl- and crotyltrifluoroborates. Scheme 5. Addition of aniline derivatives to cinnamaldehyde. predominantly more than the other. The K10 catalyzed reactions are dehydration and oxidation in the final step to deliver quinolines in good better stereoregulated with the diastereomeric ratio being greater than in to excellent yields (De Paolis et al., 2009)(Scheme 5). The reaction is the case of BF3.OEt2 catalyzed reactions. carried out under solvent-free condition and with the assistance of Montmorillonite K10 clay catalyzes the addition of aniline deriva- microwave radiation. tives to cinnamaldehyde in a Michael fashion as the first step of a A three-component reaction of enaminones, β-ketoesters/1,3- domino process involving cyclization in the second step followed by diketones and ammonium acetate takes place under the catalytic Scheme 6. Reaction of enaminones, β-ketoesters and ammonium acetate to form pyridines. G. Nagendrappa / Applied Clay Science 53 (2011) 106–138 109 Scheme 10. Addition of carbenes to C=N double bonds to produce aziridines. Scheme 7. Synthesis of ethers by the addition of alcohols to olefins. chiral bis(oxazaline)-copper (Box–Cu(II)) complexes supported on influence of montmorillonite K10 clay in refluxing isopropyl alcohol to laponite clay-like solid and Nafion-like solid (Scheme 9). The produce tri-substituted pyridines in good yields (Reddy et al., 2005c) suitability of the supported catalyst
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