Generally, the hydroboration of benzonitrile produces BN containing compound. However, an unprecedented BC bond may be formed in the presence of suitable external electric field (EEF). In reactions of benzonitrile with borane, when EEF is oriented to parallel the positive direction (N→C) of N≡C bond, the barriers of path M are decreased gradually, meaning the pathway of generating BC bond is
... [Show full abstract] easier and easier. Accordingly, EEF could influence hydroboration and control selectivity by changing its magnitude and directions.