Conversion of Alkyl Halides into the Corresponding Alcohols Under Mild Reaction Conditions

A convenient method for the synthesis of hydroxymethyl and carboxaldehyde derivatives of 3,5-diphenyl-4H-pyran-4-one

“…We performed the conversion of bromomethyl groups smoothly to hydroxymethyl groups under conditions that would not open the ring of 4H-pyran-4-one molecule. Thus, treatment of the bromomethyl derivatives, compounds 8 and 9, with silver acetate in glacial acetic acid 22 produced the corresponding acetoxymethyl derivatives, compounds 10 and 11, in 93 and 91% yields, respectively. We also achieved these conversions using potassium fluoride in acetic acid 23 in 61 and 58% yields, respectively.…”

A Novel Method for the Synthesis of 4h-Pyran-4-One Derivatives

“…15 Yields of these reactions ranged from 78 to 89%. We also obtained these conversions by potassium fluoride in acetic acid16 in 42 to 59% yields.…”

Mild and efficient capture and functionalisation of CO2 using silver(i) oxide and application to 13C-labelled dialkyl carbonates

“…Using our optimised reaction conditions in either i PrOH or BnOH, hexyl bromide gave the corresponding alkyl alcohol 5 preferentially (53-62%) with only low conversion to the carbonates 2 or 4, even at higher loadings of Ag 2 O (entries 23-25, Table 3). This is again of interest as previous methods have required high temperatures, 51,56 a two-step procedure, 52 tin 57 or HgO 58 to convert unactivated alkyl bromides to the corresponding alcohols. No reaction was observed with hexyl chloride, presumably due to a lack of reactivity as only starting material was recovered (entry 26).…”

“…This is of interest as, despite its apparent simplicity, methods to transform alkyl halides to the corresponding alcohols often result in elimination or require harsh reaction conditions. 51,52 The conversion of alkyl iodides to the corresponding alcohols using silver(I) salts have been previously reported and include Ag 2 O, 53,54 Ag 2 CO 3 55 and AgBF 4 . 52 The highest conversions to the unsymmetrical carbonate 2 were observed when the reactions were performed without additional solvents.…”