Nickel boride deselenations

Deselenation. C-Se bonds are cleaved reductively by nickel boride in methanol in generally high yield. This reduction can even be more facile than reduction of C=C bonds. 

Selenides are also nucleophilic and produce isolable selenonium salts (9) when treated with alkyl halides. They are easily oxidized to selenoxides (10) and further to selenones (11) under more forcing conditions (see Section 4). Reduction of selenides to the corresponding hydrocarbons is most conveniently achieved with nickel boride,or with tri-n-butyl- or triphenyltin hydride under radical conditions. " Other reagents for reductive deselenization include Raney nickel, lithium triethylborohydride, and lithium in ethylamine (Scheme 4). Benzylic selenides undergo radical extrusion reactions under thermal or photolytic conditions to produce... 

Nickel boride has also been found to be effective for reductive deselenation. The method is convenient for the preparation of mono-deuteriated alkanes (equation 36) . ... 

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See also in sourсe #XX -- [ ]

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