1-(4-Cyclopropylphenyl)ethanone

General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.To a solution of 1-(4-bromophenyl)ethanone (3.Og, 0.0150 mmol) in mixture of DMSO: water (3:1, 30 mL) was added tripotassium phosphate (9.5 g, 0.045 mmol), 1, 1 ‘-bi s(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane (0.200 g, 0.245 mmol) and cyclopropylboronic acid (1.9 g, 0.022 mmol). The reactionmixture was heated at 100 °C for 48 h. The reaction mass was quenched with water and extracted with EtOAc. The organic layer were washed with water and brine, dried over Na2504 and concentrated. The obtained solid was purified by column chromatography on silica gel to afford 1.0 g of the title product. ‘H NIVIR (300 IVIFIz, DMSO d6): 7.86-7.83 (d, J = 7.8 Hz, 2H), 7.13.7.10 (d, J = 7.8 Hz, 2H), 2.57 (s, 3H), 1.94 (m, 1H), 1.07-1.05 (q, J= 7.2 Hz, 2H), 0.79-0.77 (d, J= 4.8 Hz, 2H).Use of cyclopropyldioxazaborocane in the Suzuki coupling reaction; The boronic acid coupling products were obtained under the conditions recorded in the table below, by applying procedures 3a) and 3b).+ catalyst + ligand + KExample 3b): Coupling with chlorinated derivatives:; Procedure:Cyclopropyldioxazaborocane (1.5 eq.) is dissolved in a solution of 1 N HCI/NaClGeneral procedure: Method A: A sealed tube equiped with a magnetic stirring bar was charged with the arylhalide (1) or (5) (1.0 equiv), sodium carbonate (2.0 equiv), anhydrous lithium chloride (2.0equiv) and (SIPr)Pd(allyl)Cl (0.05 equiv). Tricyclopropylbismuth (2a) (1.0 equiv), preparedas described above, was dissolved in anhydrous DMF (0.1 M) under argon and was addedinto the sealed tube. Carbon monoxide was bubbled in the reaction mixture for 45 seconds, then the tube was sealed and heated at 40 °C for 16 hours. The reaction mixture was cooledto room temperature, transferred in a separatory funnel containing 20 mL of an aq. sat.NaHCO3 solution and was extracted with EtOAc (3 x 20 mL). The combined organic layerswere washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated underreduced pressure. The residue was purified by flash column chromatography using theindicated solvent system to afford the desired aryl cyclopropyl ketone (3) or (6).Method B: Same as method A except that 1.5 equivalents of tricyclopropylbismuth 2ainstead of 1.0 equivalent and 0.1 equivalents of (SIPr)Pd(allyl)Cl instead of 0.05 equivalentswere used and that the reaction was heated at 80 C instead of 40 C.

Molecular Weight:160.21
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:160.088815002
Monoisotopic Mass:160.088815002
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:173
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes