Amidomercuration alkenes

There are several methods available for the electrophilic addition of hydrogen and nitrogen to alkenes, dienes and alkynes. While the direct electrophilic addition of amines to these substrates is not feasible, aminomercuration-demercuration affords a very useful indirect approach to such amines. The addition of amides to C—C multiple bonds can be effected directly through the Ritter reaction or by the less direct, but equally useful, amidomercuration-demercuration process using either nitriles or amides. Similarly, H—N3 addition to alkenes can be carried out directly or via mercuration to produce organic azides. 

A variety of alkenes undergo successful amidomercuration, but alkenes of the type R2C CH2 and R2C=CHR fail to react in the anticipated fashion.243-245 While rearrangements have been observed with a- and fi-pinene,243 3,3-dimethyl-1 -butene reacts normally.244... 

Amides can also be utilized for amidomercuration.242248-249 The reaction is usually run using equivalent amounts of the alkene and Hg(NCb)2, plus 10 equiv. of amide in refluxing dichloromethane (equation 176). 

Amidomercuration. The reaction of alkenes with anhydrous Hg(N03)2 in the presence of primary amides in CH2C12 followed by demercuration (NaBH4-NaOH- -BuNH2) results in N-substituted amides in 45-99% yield (equation I). 

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