Abstract
The development of a new facile method for the acetylation of alcohols and carbohydrate-derived polyols is described. This method relies on the nature of the cationic palladium catalyst, Pd(PhCN)2(OTf)2 which is generated in situ from Pd(PhCN)2Cl2 and AgOTf to catalyze the acetylation reaction. This new acetylation protocol is very rapid and proceeds under mild conditions with only 1 mol% of catalyst loading at room temperature. This new method has been applied to a variety of different alcohols with different levels of steric hindrance, as well as carbohydrate-derived polyols to provide the corresponding fully acetylated products in excellent yields.
Highlights
Manipulation of functional groups through their protection and deprotection is of prime importance in organic synthesis, resulting in the eventual synthesis of bioactive and medicinally important natural products
Some notable examples include the use of tributylphosphine [6,7], bromine [8], p-Toluenesulfonic acid [9], alumina [10], scandium triflate [11], indium triflate [12,13], bismuth triflate [14], trimethylsilyl triflate [15], copper triflate [16], cerium triflate [17], ruthenium chloride [18], sulfamic acid [19], montmorillonite K-10 [20], molecular sieves [21], iron (III)chloride [22], magnesium bromide [23], tantalum chloride [24], vanadyl acetate [25], N-bromosuccinamide (NBS) [26], 3-nitrobenzeneboronic acid [27], lithium perchlorate (LiClO4 ) [28], silica gel supported sodium hydrogen sulfate [29], sodium acetate trihydrate [1], dried sodium bicarbonate [30] and Iodine [31,32]
We report a novel method that utilizes cationic palladium (II) species as acetylation alcohols and carbohydrate-derived polyols
Summary
Manipulation of functional groups through their protection and deprotection is of prime importance in organic synthesis, resulting in the eventual synthesis of bioactive and medicinally important natural products. Some notable examples include the use of tributylphosphine [6,7], bromine [8], p-Toluenesulfonic acid [9], alumina [10], scandium triflate [11], indium triflate [12,13], bismuth triflate [14], trimethylsilyl triflate [15], copper triflate [16], cerium triflate [17], ruthenium chloride [18], sulfamic acid [19], montmorillonite K-10 [20], molecular sieves [21], iron (III)chloride [22], magnesium bromide [23], tantalum chloride [24], vanadyl acetate [25], N-bromosuccinamide (NBS) [26], 3-nitrobenzeneboronic acid [27], lithium perchlorate (LiClO4 ) [28], silica gel supported sodium hydrogen sulfate [29], sodium acetate trihydrate [1], dried sodium bicarbonate [30] and Iodine [31,32] While these methods provides viable alternative for acetylating alcohols, some of these methods utilizes catalysts that are expensive, moisture sensitive, require long reaction times and tedious work-up protocols and sometimes result in low yields. Catalyst in the acetylation of alcohols and carbohydrate-derived polyols
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