1-Iodonaphthalene

clear yellow to brown liquid

General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBrGeneral procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–vGeneral procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol, ), (CFGeneral procedure: 0.05 mmol Cu(NOGeneral procedure: Aryl bromide (10 mmol) was dissolved in dry THF (30 mL) and cooled to -78 °C under anargon atmosphere. n-Butyllithium (1.6 M in n-hexane; 7.5 mL; 12 mmol) was addeddropwise. After 15 minutes a solution of I2 (3.81 g; 15 mmol) in dry THF (10 mL) was addedand the reaction mixture was allowed to warm to room temperature overnight.For workup the reaction mixture was concentrated in vacuo. H2O was added to the residueand it was extracted with DCM (3x). The combined organic phases were washed withsaturated Na2S2O5 solution and H2O. After drying over MgSO4 and concentration underreduced pressure, the crude product was purified by column chromatography.General procedure: A Schlenk tube was charged with Cu2O (7.2 mg, 10 molpercent), l-proline (11.5 mg, 20 molpercent), aryl (or heteroaryl) bromide (1 or 3, 0.50 mmol), potassium iodide (KI) (249 mg, 0.75 mmol), and EtOH(1.5 mL) under nitrogen atmosphere. The Schlenk tube was sealedwith a teflon valve, and then the reaction mixture was stirred at110C for a period (the reaction progress was monitored by GCanalysis). After the reaction was completed, GC yield of high volatileproduct was determined using an appropriate internal standard(chlorobenzene or 1-chloro-4-methylbenzene) or the solvent wasremoved under reduced pressure. The residue obtained was puri-fied via silica gel chromatography (eluent: petroleum ether/ethylacetate = 10/1) to afford aryl iodides 2a–2o or heteroaryl iodides4a–4g.General procedure: To a solution of trifluoroborate (1 mmol) in 3 mL of aqueous DMF (2:1 v/v), cesium triiodide (1 mmol) was added. The mixture was stirred at 80 °C for the appropriate time (Table 3) and then diluted with 10 mL of ether. The aqueous layer was extracted twice with ether (5 mL) and the combined organic phase was dried over anhydrous Na

For organic synthesis

Molecular Weight:254.07
XLogP3:4.2
Exact Mass:253.95925
Monoisotopic Mass:253.95925
Heavy Atom Count:11
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes