* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With palladium diacetate; triethylamine; In neat (no solvent); at 150℃; for 0.0833333h;Microwave irradiation; Green chemistry;
General procedure: To0.21 ml (2.0 mmol) of bromobenzene was added 3.0 mmol of dialkyl phosphite[0.39 ml of diethyl phosphite (1a) or 0.59 ml of dibutyl phosphite (1b)], or2.0 mmol of ethyl phenylphosphinate (1c) (0.30 ml), or diphenylphosphineoxide (1d) (0.40 g), 0.31 ml (2.2 mmol) of Et3N and 0.022 g (0.10 mmol) [or0.014 g (0.06 mmol)] of Pd(OAc)2, and the resulting mixture was irradiated in aclosed vial in a CEM Discover (300 W) microwave reactor at the temperatureand for the time shown in Table 1. The mixture was passed through a thin (ca.1-1.5 cm) layer of silica gel using EtOAc. Volatile components were removed invacuo to give the products as oils (2a-c), or as crystals (2d). Mp for 2d: 156 C,mp14d: 156.6-157.4 C.
28%
With [2,2]bipyridinyl; triethylamine; nickel dichloride; zinc; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere;
General procedure: To an eggplant flask was added H-phosphinate 2a (86.5 mg,0.509 mmol), NiCl2 (7.7 mg, 0.0509 mmol), 2,2`-bipyridine (17.1 mg,0.109 mmol), triethylamine (142 mL, 1.02 mmol), zinc dust (43.2 mg, 0.610 mmol), iodobenzene 1a (68.0 mL, 0.610 mmol) and dry DMF (1.0 mL) under Ar. Then the mixture was stirred at 50 C for 24 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/EtOAc 1:1) to give 3a (118 mg, 94%).
With [2,2]bipyridinyl; triethylamine; nickel dichloride; zinc; In N,N-dimethyl-formamide; at 50℃; for 24h;Inert atmosphere;Catalytic behavior;
To an eggplant flask was added H-phosphinate 2a (86.5 mg,0.509 mmol), NiCl2 (7.7 mg, 0.0509 mmol), 2,2`-bipyridine (17.1 mg,0.109 mmol), triethylamine (142 mL, 1.02 mmol), zinc dust (43.2 mg, 0.610 mmol), iodobenzene 1a (68.0 mL, 0.610 mmol) and dry DMF (1.0 mL) under Ar. Then the mixture was stirred at 50 C for 24 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/EtOAc 1:1) to give 3a (118 mg, 94%).
With caesium carbonate; cesium fluoride; In acetonitrile; at 100℃; for 12h;Sealed tube;
General procedure: In a typical reaction, to an oven-dried 25 mL heavy walled sealtube fitted with Teflon plug valve was added CsF (0.60 mmol),Cs2CO3 (0.90 mmol), o-(trimethylsilyl)aryl triflate (0.30 mmol) anddialkyl phosphate (0.32 mmol). MeCN (3 mL) was added via a syringe. The tube was sealed with Teflon plug valve and then thereaction mixture was stirred at 100 C for 12 h. The reaction wasallowed to cool to room temperature. Then reaction mixture wasdiluted with 5 mL water. The aqueous layer was extracted withethyl acetate (35 mL). The combined organic layers were driedover Na2SO4, filtered and concentrated. The product was isolatedthrough preparative thin-layer chromatography.