Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[C:10]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=2)[CH:7]=[O:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
A mixture of commercially available 5-bromonicotinaldehyde (5.070 g; 26.43 mmol), phenylboronic acid (4.934 g; 39.65 mmol), and Pd(PPh3)4 (1.527 g; 1.32 mmol) in toluene (65 ml) and aq. 2 M Na2CO3 (59 ml) was heated to reflux, under nitrogen, for 2.5 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=1/1) afforded 5-phenylnicotinaldehyde as a yellow oil. LC-MS (conditions A): tR=0.61 min.; [M+H]+: 184.48 g/mol.
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