Sodium cyanoborohydride alkyl halides

REDUCTION OF ALKYL HALIDES AND TOSYLATES WITH SODIUM CYANOBOROHYDRIDE IN HEXAMETHYL-PHOSPHORAMIDE (HMPA) A. 1-IODODECANE TO n—DECANE B. 1-DODECYL TOSYLATE TO n-DODECANE, 53, 107 REDUCTION OF KETONES BY USE OF TOSYLHYDRAZONE DERIVATIVES ANDROSTAN-17 0—OL, 52, 122 REDUCTIVE AMINATION WITH SO-... [Pg.135]

Tributyltin hydride, 316 Zinc iodide, 280 From alkyl halides Lithium aluminum hydride-Ceri-um(III) chloride, 159 Palladium catalysts, 230 Sodium cyanoborohydride-Tin(II) chloride, 280 From alkyl sulfonates Lithium triethylborohydride, 153 From thiols... [Pg.381]

REDUCTION OF ALKYL HALIDES AND TOSYLATES WITH SODIUM CYANOBOROHYDRIDE IN HEXAMETHYLPHOS-PHORAMEDE (HMPA) ... [Pg.107]

These preparations that illustrate the use of sodium cyanoborohydride in hexamethylphosphoramide as an effective, selective, and convenient procedure for the reduction of alkyl halides and tosylates is essentially the same as previously described.8 The very mild reducing ability of sodium cyanoborohydride makes the method particularly valuable when other functional groups are present in the molecule... [Pg.109]

Reduction of alkyl halides and tosylates. - Reduction with sodium cyanoborohydride in HMPT provides a rapid and selective removal of iodo. bromo, and tosyloxy groups in high yield. Thus 1-iododecane can be reduced in thi.s way to n-deeane in... [Pg.448]

Na(BH3CN] (sodium cyanoborohydride) Alcohols, water, DMSO 0 to RT ketone —> alcohol aldehyde —> alcohol alkyl halide —> alkane imine —> amine... [Pg.281]

Cyanoborohydride and its modified reagents have been used for reductive dehalogenations. Thus, the combination of sodium or tetrabutylammonium cyanoborohydride, sodium or potassium 9-cyano-9-hydro-9-borabicyclo[3.3.1]nonanate [9-BBNCN] (2) or polymeric cyanoborane (3) in HMPA furnishes an efficient and mild system for the reduction of alkyl halides. The reagents are selective in that other functional groups, including ester, carboxylic acid, amide, cyano, alkene, nitro, sulfone, ketone, aldehyde and epoxide, are essentially inert under the reduction conditions thus, the reduction procedure is attractive for synthetic schemes which demand minimum damage to sensitive portions of the molecule. [Pg.806]

Reactions.—New systems for the reduction of alkyl halides to alkanes include mixtures of lithium aluminium hydride with transition-metal chlorides (such as Ni or Co" chlorides) and some complex metal hydrides of copper, especially the THF-soluble Li4CuHs. Details of the application of sodium cyanoborohydride to the reduction of halides (and sulphonate esters) in dipolar aprotic solvents have been published. Virtually all other functional groups are inert to this convenient, mild, and efficient system, which has been used to develop a one-pot deoxygenation of primary alcohols (Scheme 39) via the iodides. The alternative cyanoborohydride reagents (55) and the polymeric (56) are also discussed. ... [Pg.130]

Big Chemical Encyclopedia

Chemical substances, components, reactions, process design ...