By Peter J. H. Scott
Integrates solid-phase natural synthesis with palladium chemistry
The Wiley sequence on Solid-Phase natural Syntheses retains researchers present with significant accomplishments in solid-phase natural synthesis, delivering complete experimental information. Following the confirmed, demonstrated, and confirmed experimental strategies, readers can simply practice a huge variety of advanced syntheses wanted for his or her personal experiments and business purposes. The sequence is with ease equipped into themed volumes in keeping with the categorical kind of synthesis.
This moment quantity within the sequence makes a speciality of palladium chemistry in solid-phase synthesis, exploring palladium catalysts and reactions, systems for training and usage, ligands, and linker reactions. the 1st a part of the quantity bargains a finished evaluation of the sector. subsequent, the chapters are prepared into 3 parts:
- Part : Palladium-Mediated Solid-Phase natural Syntheses
- Part 3: Immobilized Catalysts and Ligands
- Part 4: Palladium-Mediated Multifunctional Cleavage
Each bankruptcy is written by way of a number of best overseas specialists in palladium chemistry. Their contributions replicate an intensive exam and evaluate of the present literature in addition to their very own first-hand laboratory adventure. References on the finish of every bankruptcy function a gateway to the field's literature.
The creation of palladium-mediated, cross-coupling reactions greater than thirty years in the past revolutionized the technology of carbon-carbon bond formation. It has now develop into a cornerstone of state-of-the-art artificial natural chemistry laboratory. With this quantity, researchers in natural and medicinal chemistry have entry to a unmarried source that explains the basics of palladium chemistry in solid-phase synthesis and units forth transparent, step by step directions for carrying out their very own syntheses
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Extra info for Solid-Phase Organic Syntheses, Solid-Phase Palladium Chemistry
A general method to protect carboxylic acids as their allyl ester group on solid support is described in Route 2. 6. The synthesis, cleavage, and analysis can be carried out manually or automated using combichem processes. REFERENCES 1. Lee H, Sarko CR. Analysis of a combinatorial library synthesized using a split-and-pool Irori MicroKan method for development and production. In: Kyranos JN High throughput analysis for early drug discovery. San Diego, CA: Elsevier; 2004. pp. 37–56. 2. Guib´e F.
Kaval N, Dehaen W, Van der Eycken E. J Comb Chem 2005;7:90. 6. Appukkuttan P, Van der Eycken E. Eur J Org Chem 2008;E:1133. 7. (a) Prokopkova H, Kappe C. O. Angew Chem Int Ed 2009;48:2276 references cited therein; (b) Liebeskind L. S, Sorgl J. J Am Chem Soc 2000;122:11260–11261. 8. (a) Singh B. K, Parmar V. S, Van der Eycken E. Synlett 2008;21:3021; (b) Singh B. K, Mehta V. P, Parmar V. S, Van der Eycken E. Org Biomol Chem 2007;5:2962; (c) Singh B. K, Appukkuttan P, Claerhout S, Parmar V. S, Van der Eycken E.
MS (CI): m/z (%) = 308 (100) [M + H+ ]. Compound 12. 5-Chloro-3-phenyl-1-(4-methoxybenzyl)-2(1H )-pyrazinone. 79 (s, 3H). 48. 0817. MS (CI): m/z (%) = 329 (45) [M + H+ ], 121 (100) (PMB). NOTES 1. Dichloromethane (CH2 Cl2 ), tetrahydrofuran (THF), methanol (MeOH), dimethylformamide (DMF), toluene, trimethylsilyl cyanide (TMSCN), benzaldehyde, oxalyl chloride, diisopropyl ethylamine (Hunig’s base, DIPEA), triﬂuoroacetic acid (TFA), triethyl silane (TES), hexane, ethyl acetate (EtOAc), palladium(0) tetrakistriphenyl phosphine [Pd(PPh3 )4 ], palladium(II) diphenylphosphino dichloride [Pd(PPh3 )2 Cl2 ], Cu(I) iodide, phenylboronic acid, phenylacetylene, tetraphenyl tin (Ph4 Sn), copper(I) thiophene-2-carboxylate (CuTC), sodium carbonate (Na2 CO3 ), and potassium carbonate (K2 CO3 ) were purchased from Acros Organics and were used as available.