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42.12.2.1.1.1 Variation 1: Addition of Phosphines to Aldehydes or Ketones

DOI: 10.1055/sos-SD-042-00526

Virieux, D.; Volle, J.-N.; Pirat, J.-L.Science of Synthesis, (200942509.

(α-Hydroxyalkyl)phosphonium salts 13 are classically obtained by nucleophilic addition of phosphine (PH3),[‌44‌] primary,[‌45‌‌48‌] secondary,[‌45‌] or tertiary phosphines[‌49‌‌52‌] to aldehydes or ketones in the presence of acids, in order to avoid the reverse reaction (Scheme 11). When anhydrous conditions are required, dry hydrogen bromide is generated in situ by the reaction of bromine with acetone. In this case, the latter reagent is also acting as the carbonyl reagent.[‌52‌] The reaction has also been carried out on substrates containing more than one phosphorus group,[‌46‌,‌47‌] a bulky (3,3-dimethylbicyclo[2.2.1]hept-2-yl)methyl substituent,[‌48‌] or more than one substituent type.[‌51‌]

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