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1-(8-naphthyl)-isoquinoline (8-NAIQ). 1-(8-naphthyl)-isoquinoline was obtained from thereaction of <strong>[63927-22-0]8-bromoisoquinoline</strong> and naphthalene-1-boronic acid by Suzuki coupling [8].
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 1-(7-benzofuranyl)-2-di(3,5-di-tert-butyl-4-methoxyphenyl)phosphinenaphthalene; In toluene; at 80℃; for 10h;Glovebox; Inert atmosphere;
In a glove box, 1.0 mmol of a halogenated aromatic or heterocyclic aromatic hydrocarbon compound, 2.0 mmol of 1-naphthylboronic acid, Pd2 (dba) 3, a phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen,After heating to 80 ° C, the reaction was carried out for a period of time. The results are shown in Table 1. The amount of Pd2 (dba) 3 and the phosphine ligand is divided into three types: (1) 0.25 molpercent Pd2 (dba) 3, 0.5 molpercent phosphine ligand, or (2) 0.5 molpercent Pd2 (dba) molpercent phosphine ligand, or (3) 1.0 molpercent Pd2 (dba) 3, 2.0 molpercent phosphine ligand, depending on the amount of ligand used in Table 1.
81%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); C38H31O5P; In toluene; at 80℃; for 8h;Inert atmosphere; Glovebox;
General procedure: In the glove box, Sm5 (0.1 mmol, 1.0 equiv), Sm2 (0.2 mmol, 2.0 equiv), K3PO4 (0.3 mmol, 3.0 equiv), Pd2(dba)3 (1.0percent mmol), (±)-8A (2.0percent mmol) and toluene (4.0mL) were added into a 25 mL single-necked flask, the reaction was stirred at 80 deg. C under nitrogen for 8 hours.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene;Inert atmosphere; Reflux;
A Straus flask equipped with a stirrer bar was charged with 2-bromopyridine (1.0 equiv.), 1-naphthylboronic acid (1.1 equiv),Pd(PPh3)4 (4 mol%), 2 M aq Na2CO3 (2.5 mL/mmol), toluene(3.8 mL/mmol), and ethanol (1.3 mL/mmol). The mixture wasdegassed by three freeze-pump-thaw cycles and then refluxedunder inert conditions overnight. The mixture was cooled to r.t.and extracted with EtOAc (3 × 20 mL). The organic phases werecombined, dried (MgSO4), and concentrated. The pure ligandwas obtained by flash column chromatography [silica gel,EtOAc-hexane (1:4)].Compound was isolated as viscous liquid that solidified uponstanding. Yield: 1.6 g (99%).
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