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37.8.2.1.2.3 Variation 3: Using Benzyl Halides and Silver(I) Oxide

DOI: 10.1055/sos-SD-037-00601

Petursson, S.Science of Synthesis, (200837860.

It is not surprising that Purdies silver(I) oxide catalyst has been used for benzylations. Kuhn used this method in dimethylformamide for the benzylation of 1,2:5,6-di-O-isopropylidene-α-d-glucose with both benzyl chloride and benzyl bromide.[‌52‌] A more recent use of silver(I) oxide catalysis for benzylation uses toluene or dichloromethane as solvent.[‌53‌] Symmetrical diols give almost exclusively monoalkylation, but regioselectivity is low. The general equation is given in Table 2, along with results from selected examples; a typical procedure follows.

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