Benzene → 5-Phenylpyridine-2-carbonitrile

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1>C(P[Pd](PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>[C:10]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1