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Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2’-bipyridine In hexane at 60℃; for 0.5h; Inert atmosphere; Glovebox; Sealed tube;
Stage #2: N,N-diethyl-2-pyridinecarboxamide With bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In hexane at 20℃; for 18h; Sealed tube;
47%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 80℃; for 18h; Inert atmosphere; Sealed tube; regioselective reaction;
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In 1,2-dichloro-ethane; at 120℃; for 24h;Schlenk technique; Inert atmosphere;
General procedure: N,N-Diethylpicolinamide (1; 0.2 mmol, 1.0 equiv), [Cp*RhCl2]2 (0.005 mmol, 2.5 mol%), AgSbF6 (0.02 mmol, 10 mol%), Cu(OAc)2 (0.4 mmol, 2.0 equiv), alkyne 2 (0.44 mmol, 2.2 equiv) and DCE (2 mL) were added to a 20-mL Schlenk tube. After being purged with nitrogen, the mixture was stirred at 120 C for 24 h. Then concd aq NH3 (2 mL) was added and stirred for 5 min. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on silica gel to afford isoquinoline 3.
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In 1,2-dichloro-ethane; at 120℃; for 24h;Schlenk technique; Inert atmosphere;
General procedure: N,N-Diethylpicolinamide (1; 0.2 mmol, 1.0 equiv), [Cp*RhCl2]2 (0.005 mmol, 2.5 mol%), AgSbF6 (0.02 mmol, 10 mol%), Cu(OAc)2 (0.4 mmol, 2.0 equiv), alkyne 2 (0.44 mmol, 2.2 equiv) and DCE (2 mL) were added to a 20-mL Schlenk tube. After being purged with nitrogen, the mixture was stirred at 120 C for 24 h. Then concd aq NH3 (2 mL) was added and stirred for 5 min. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on silica gel to afford isoquinoline 3.
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