Synthesis of Achiral Nitriles

The B-R-9-BBN reacts with chloroacetonitrile [1] under the influence of potassium 2,6-di-t-butylphenoxide to produce the corresponding nitriles in high yield (Eq. 10.1). The reaction intermediate undergoes protonolysis readily and without adding ethanol or other protonolyzing agent as required, for example, in the synthesis of ketones under similar conditions. 

The reaction is extended to the synthesis of a-chloronitriles and dialkylaceto-nitriles [2]. Monoalkylation of dichloroacetonitriles with 1 equiv of B-R-9-BBN proceeds nicely under the influence of 2,6-di-terf-butylphenoxide to afford the a-chloronitriles in satisfactory yields (Eq. 10.2 Table 10.2) [2]. 

The reaction is also highly satisfactory for introduction of two alkyl groups. The two identical alkyl groups are introduced by utilizing 2 mol of base and 2 mol of the organoborane. Alternatively the dialkylacetonitriles with different alkyl groups are easily obtained in two successive monoalkylations (Chart 10.1) [2]. 

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