Representative experimental procedures

General procedure 2, copper metal-catalyzed synthesis of 1,2,3-triazoles [6, 23]. Phenylacetylene (2.04g, 20mmol) and 2,2-bis(azidomethyl)propane-l,3-diol (1.86g, lOmmol) were dissolved in 1 2 tert-butanol/water mixture (50mL). About 1 g of copper metal turnings was added, and the reaction mixture was stirred for 24 h, after which time TLC analysis indicated complete consumption of starting materials. Copper was removed, and the white product was filtered off, washed with water, and dried to yield 3.85 g (98%) of pure bis-triazole product. 

General procedure 3, general hioconjugation procedure in aqueous buffer [88]. The example here is generalized to a biomolecule-alkyne and a cargo-azide, where the biomolecule can be peptide, protein, or polynucleotide, and the cargo can be any small- or large-molecule moiety that the user wishes to couple to the biomol- 

ZnBrj (2.76g, 12.28 mmol) in THF (10 ml) at 0°C. The first reaction mixture was then transferred through a cannula to the second flask, and [PdCljIdppf)] (317mg, 

37 mmol) was added. The reaction mixture was then heated to reflux for 10 h, diluted with Et20, washed with aqueous NH4CI and then with aqueous NaHCOj. 

The combined organic layers were dried over MgS04, filtered, and concentrated. Chromatography on silica gel (hexane/EtOAc, 90 10) afforded the title compound (2.08 g, 87%). Note The title compound was further converted to ( )-y-bisabolenes with 98% purity in three steps. 

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Representative Experimental Procedures 128 Representative Procedure for Preparation of Cl-Hemiacetal Donors Through a Peracylation-Selective Anomeric Deacylation Sequence 128... 

The preparative methods are outlined in sequence and representative experimental procedures are described in later chapters. 

REPRESENTATIVE EXPERIMENTAL PROCEDURES Historically Important Procedures... 

REPRESENTATIVE EXPERIMENTAL PROCEDURES 16.5.1. Reactions in Liquid Ammonia... 

For a representative experimental procedure, see Erker, G. in Houhen-Weyl, Vol. E18, Part 2 p868 (1986). 

The representative experimental procedure is as follows 1,4-dibromobutane (1 mmol, 0.215 g) and sodium azide (2.5 mmol, 0.163 g) in water (2 mL) were placed in a 10 mL crimp-sealed thick-walled glass tube equipped with a pressure sensor and a magnetic stirrer. The reaction tube was placed inside the cavity of a CEM Discover focused microwave synthesis system, operated at 120 + 5°C (temperature monitored by a built-in infrared sensor), power 70-100 Watt and pressure 60-100 psi, for 30 minutes. After completion of the reaction, diethyl ether was added to extract the alkyl azide. GC/MS analysis indicated the disappearance of alkyl halides. FT-IR spectrum of crude product was obtained using a FT-IR spectrometer and the formation of alkyl azide was confirmed by the characteristic IR adsorption around 2100 cm Removal of the solvent under reduced pressure (rotary evaporator) afforded the product, 1,4-diazido-butane (0.125 g) in 89% yield. 

A wide range of experimental conditions for the CuAAC have been employed since its discovery, underscoring the robustness of the process and its compatibility with most functional groups, solvents, and additives, regardless of the source of the catalyst. The most commonly used protocols and their advantages and limitations are discussed below, and representative experimental procedures are described at the end of this chapter. 

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