Sodium Iodide

(A) Möker and Thiem showed that the 4′-chloro substituent of the 6- O-(4′-chlorobutyl)-1,2:3,4-di-O-isopropylidene-a-D-galactopyranose was replaced by iodide in acetone under reflux for 24 h in a Finkelstein reaction o give the product 3-O-(4′-iodobutyl)-1,2:5,6-di-Oisopropylidene- a-D-glucofuranose in 85% yield. Figure represented (B) Eras et al. reported that 0.5 equivalent of sodium iodide (NaI) in butanone and the presence of a reducing agent like sodium thiosulfate induce the formation of the corresponding allyl esters 2, starting from 2-chloro-1-(chloromethyl)ethyl alkyl or aryl esters 1 by the Finkelstein rearrangement-elimination reaction. Figure represented (C) Meyer and Hergenrother described the synthesis of 2,3-disubstituted naphthalene by Diels-Alder aromatization reaction between α, α, α′, α ″-tetrabromo o-xylene and a 2-pentanone derivative in the presence of sodium iodide in DMF. Figure represented (D) Recently, Firouzabadi et al. reported a new environmentally friendly catalytic method for the efficient monoiodination of arenes. The method is based on using sodium iodide, hydrogen peroxide (35%) and cerium(III) chloride as an effective catalyst in water under reflux conditions. This method can also be applied easily in the syntheses of iodinated cyclic ethers and iodinated lactones from their corresponding unsaturated alcohols and carboxylic acids in high yield. Figure represented (E) A new method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides utilizing NaI, a catalyst system comprising CuI and a 1,2- or 1,3-diamine ligand was developed by Klapars and Buchwald. This method gives products in excellent yield. Figure represented (F) Bartoli and co-workers described a simple and efficient method of converting azides into exclusively primary amines using NaI in the presence of inexpensive CeCl3·7H2O in refluxing acetonitrile or under microwave-assisted irradiation. Figure represented (G) Bartoli and co-workers have also reported the hetero-Michel addition of nucleophilic nitrogen compounds to electron-poor alkenes promoted by the CeCl3·7H2O/NaI system supported on alumina under solvent-free conditions. The resulting b-amino derivatives are versatile synthons for the synthesis of many nitrogen-containing biologically important compounds. © Georg Thieme Verlag Stuttgart New York.