α-Arylation and alkynylation of cyclic -iodoenones using palladium-catalyzed cross-coupling reactions with trifluoroborate salts

Synlett

Volumn , Issue 3, 2010, Pages 427-432

  Gueogjian, Kemilla ^a   Singh, Fateh V ^a   Pena, Jesus M ^a   Amaral, Monica F Z J ^a   Stefani, Hélio A ^a,b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

substituted enones; Cross coupling reaction; Cyclic iodoenones

Indexed keywords

2 CYCLOHEXENONE; ALPHA IODOENONE; BORIC ACID; CHEMICAL COMPOUND; PALLADIUM; POTASSIUM; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTRON; SYNTHESIS;

EID: 76249124587     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218580     Document Type: Article

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50. General Procedure for the Cross-Coupling Reaction of Aryltrifluoroborate Salts with 2-Iodocyclohex-2-enone (Table 3, Entry 1) To a round-bottomed flask containing phenyltrifluoroborate salt (0.5 mmol), 2-iodocyclohex-2-enone (0.5 mmol), K2CO3 (1.5 mmol), and PdCl2 (5 mol%) was added a mixture of 1,4-dioxane (4 mL) and degassed H2O (1.0 mL). The reaction mixture was allowed to stir at 80 C for 5 h. After this time, the mixture was cooled to r.t., diluted with EtOAc (10 mL), and washed with sat. aq NH4Cl (3-10 mL). The organic phase was separated, dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexaneEtOAc (8:2) as the eluent. Selected Spectral and Analytical Data for 2-Phenylcyclohex- 2-enone (4a) Yield 80%. 1H NMR (300 MHz, CDCl3): d = 7.287.40 (m, 5 H), 7.06 (t, 1 H, J = 4.1 Hz), 2.532.64 (m, 4 H), 2.092.17 (m, 2 H). 13C NMR (75 MHz, CDCl3): d = 197.9, 147.9, 140.3, 136.5, 128.5, 127.9, 127.5, 39.0, 26.5, 22.9. LRMS: m/z (%) = 172 (100) [M+], 144 (64), 130 (26), 115 (82), 103 (16), 71 (12), 63 (14), 51 (15). IR (KBr): n = 1662, 2933, 3016 cm1. Mp 9394 C (lit.13 9293 C).
51. General Procedure for the Cross-Coupling Reaction of Alkynyltrifluoroborate Salts with 2-Iodocyclohex-2- enone (Table 4, Entry 1) To a round-bottomed flask containing phenylethynyltrifluoroborate salt (0.5 mmol), 2-iodocyclohex-2-enone (0.5 mmol), K2CO3 (1.5 mmol), and PdCl2 (5 mol%) was added a mixture of 1,4-dioxane (4 mL) and degassed H2O (1.0 mL). The reaction mixture was allowed to stir at 80 C for 7 h. After this time, the mixture was cooled to r.t, diluted with EtOAc (10 mL), and washed with sat. aq NH4Cl (3-10 mL). The organic phase was separated, dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexaneEtOAc (8:2) as the eluent. Selected Spectral and Analytical Data for 2-(Phenylethynyl) cyclohex-2-enone (6a) Yield 73%. 1H NMR (300 MHz, CDCl3): d = 7.617.64 (m, 2 H), 7.247.38 (m, 3 H), 6.47 (t, J = 1.89 Hz, 1 H), 2.48 2.57 (m, 2 H), 2.342.44 (m, 2 H), 1.891.98 (m, 2 H). 13C NMR (75 MHz, CDCl3): d = 171.5, 153.3, 150.7, 131.4, 128.6 (2 C), 127.2, 123.7 (2 C), 122.4, 105.6, 62.4, 32.5, 23.0, 21.0. LRMS: m/z (%) = 196 (100) [M+], 167 (44), 152 (17), 118 (19), 95 (22), 83 (27), 77 (16).
52. General Procedure for the Cross-Coupling Reaction of Phenyltrifluoroborate Salt with 2-Iodoen-2-ones (Table 5, Entry 1) To a round-bottomed flask containing phenyltrifluoroborate salt (0.5 mmol), (S)-1-benzoyl-5-iodo-2-isopropyl-2,3- dihydropyrimidin-4 (1H)-one (0.5 mmol), K2CO3 (1.5 mmol), and PdCl2 (5 mol%) was added a mixture of 1,4- dioxane (4 mL) and degassed H2O (1.0 mL). The reaction mixture was allowed to stir at 80 C for 2 h. After this time, the mixture was cooled to r.t., diluted with EtOAc (10 mL), and washed with sat. aq NH4Cl (3-10 mL). The organic phase was separated, dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexaneEtOAc (8:2) as the eluent. Selected Spectral and Analytical Data for (S)-1-Benzoyl- 2-isopropyl-5-phenyl-2, 3-dihydropyrimidin-4 (1H)-one (8a) Yield 65%. 1H NMR (300 MHz, CDCl3): d = 7.487.59 (m, 6 H), 7.42 (dd, J = 7.5, 1.3 Hz, 2 H), 7.277.34 (m, 3 H), 6.66 (d, J = 4.4 Hz, 1 H), 5.67 (s, 1 H), 2.362.43 (m, 1 H), 1.09 (d, J = 6.7 Hz, 3 H), 1.01 (d, J = 6.9 Hz, 3 H). 13C NMR (75 MHz, CDCl3): d = 168.4, 163.4, 134.3, 133.4, 132.9, 131.4, 128.6 (2 C), 128.2 (2 C), 128.1 (2 C), 128.0, 127.5 (2 C), 116.6, 68.9, 32.8, 18.2, 17.4. LRMS: m/z (%) = 320 (1) [M+], 277 (14), 105 (100), 89 (2), 77 (28), 51 (4), 43 (2). IR: n = 3396, 3053, 2992, 2859, 1652, 1607 cm1. Mp 173.2 174.8 C.