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Synthesis of (saturated) alcohols

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Ionic liquids enhanced the nucleophilicity of water and reduced the formation of elimination products in the nucleophilic hydroxylation of alkyl halides. The reactivity of other nucleophiles such as alcohols, phenol, and acetic acid in an ionic liquid was also investigated.
D. W. Kim, D. J. Hong, J. W. Seo, H. S. Kim, H. K. Kim, C. E. Song, D. Y. Chi, J. Org. Chem., 2004, 69, 3186-3189.

Convenient methods for the preparation of stable and non-volatile mono- and dichloroborane adducts of dioxane from dioxane-BCl₃ and NaBH₄ in the presence of catalytic amounts of tri- or tetraglyme were developed. The dioxane-monochloroborane adduct hydroborates representative olefins cleanly and rapidly and lead to the corresponding alcohols in quantitative yields after oxidation.
J. V. B. Kanth, H. C. Brown, J. Org. Chem, 2001, 66, 5359-5365.

The use of Oxone allows the conversion of various aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates into the corresponding oxidized products in excellent yields. This method tolerates a broad range of functional groups, and in secondary alkyl substrates it was demonstrated to be completely stereospecific.
G. A. Molander, L. N. Cavalcanti, J. Org. Chem., 2011, 76, 623-630.

Using commercially available Ph₃PAuCl and readily prepared, benign arylsilanes, a gold-catalyzed oxyarylation of alkenes proceeds smoothly in air. The oxidant, Selectfluor, not only facilitates entry to the Au(I/III) manifold but also provides a fluoride anion for silane activation, thereby avoiding the need for addition of a stoichiometric base.
L. T. Ball, M. Green G. C. Lloyd-Jones, C. A. Russel, Org. Lett., 2010, 12, 4724-4727.

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By careful selection of appropriate enzymes (alcohol dehydrogenases [ADH] and cofactor recycling enzymes), cofactor recycling of NADH can be performed in the presence of NADP⁺ recycling to achieve overall (R)- or (S)-selective deracemisations of sec-alcohols or stereoinversion representing a possible concept for a “green” equivalent to the chemical-intensive Mitsunobu inversion.
C. V. Voss, C. C. Gruber, K. Faber, T. Knaus, P. Macheroux, W. Kroutil, J. Am. Chem. Soc., 2008, 130, 13969-13972.

A highly efficient dynamic kinetic resolution (DKR) of secondary alcohols at room temperature was developed. In situ racemization of substrates using a Ru catalyst and lipase-catalyzed acylation provides enantiopure products in high yields in very short reaction times. The use of isopropenyl acetate as the acyl donor makes the purification of the products very easy.
B. Martin-Matute, M. Edin, Krisztian Bogar, J.-E. Baeckvall, Angew. Chem. Int. Ed., 2004, 43, 6535-6539.

Well-defined 16-electron ruthenium complexes bearing an N-heterocyclic carbene ligand are active catalysts in the racemization of chiral alcohols. Mechanistic considerations are presented.
J. Bosson, S. P. Nolan, J. Org. Chem., 2010, 75, 2039-2043.