Facile One-Pot Two-Step Hydroxylation of Alkyl Halides and Alkyl Sulfonates via Acetate Intermediates

Hydroxylation of primary and secondary alkyl halides and alkyl sulfonates was readily achieved by one-pot two-step reaction under mild condition. Less reactive chloride and secondary mesylate functionalities were also transformed to hydroxide group in high yields. When 5% water-containing DMSO solvent was used, catalytic cycle of two-step hydroxylation smoothly proceeded in the presence of catalytic amount of acetate anion.

[1]  Dong Wook Kim,et al.  Hydroxylation of alkyl halides with water in ionic liquid: significantly enhanced nucleophilicity of water. , 2004, The Journal of organic chemistry.

[2]  E. Vedejs,et al.  Oxazolium-derived azomethine ylides. External oxazole activation and internal dipole trapping in the synthesis of an aziridinomitosene. , 2000, The Journal of organic chemistry.

[3]  J. Alexander,et al.  A Convenient Method for the Conversion of Halides to Alcohols , 1995 .

[4]  Yoshihiko Ito,et al.  Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition-metal complexes. 6. Practical asymmetric synthesis of 1,1'-binaphthyls via asymmetric cross-coupling with a chiral [(alkoxyalkyl)ferrocenyl]monophosphine/nickel catalyst , 1988 .

[5]  S. Gould,et al.  Synthesis of chirally deuteriated phthalimido-propanols and evaluation of their absolute stereochemistry , 1988 .

[6]  H. Reich,et al.  Hypervalent organoiodine chemistry. Syn elimination of alkyl iodoso compounds , 1978 .

[7]  H. Simmons,et al.  Crown ether chemistry. Substitution reactions of potassium halide and potassium hydroxide complexes of dicyclohexyl-18-crown-6 , 1974 .

[8]  C. Liotta,et al.  Chemistry of naked anions. I. Reactions of the 18-crown-6 complex of potassium fluoride with organic substrates in aprotic organic solvents , 1974 .

[9]  C. M. Starks,et al.  Phase-transfer catalysis. II. Kinetic details of cyanide displacement on 1-halooctanes , 1973 .

[10]  Harold S. Hill,et al.  STUDIES ON REACTIONS RELATING TO CARBOHYDRATES AND POLYSACCHARIDES. VII. THE EASE OF FORMATION AND NATURE OF CERTAIN SIX, SEVEN, AND LARGER CARBON-OXYGEN CYCLIC STRUCTURES , 1923 .

[11]  Luigi Cassar,et al.  Phase-Transfer Catalysis , 1977 .

[12]  Charles M. Starks,et al.  PHASE – TRANSFER CATALYSIS. I. HETEROGE NEOUS REACTIONS INVOLVING ANION TRANSFER BY QUATERNARY AMMONIUM AND PHOSPHONIUM SALTS , 1971 .

[13]  S. Searles,et al.  Reactions of Alcohols and Phenols with Trimethylene Oxide1 , 1954 .