A convenient method for preparing aromatic ketones from acyl chlorides and arylboronic acids via Suzuki-Miyaura type coupling reaction

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 271-273

  Urawa, Yoshio ^a,b   Ogura, Katsuyuki ^b  

^a EISAI CO LTD   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CHLORIDE; KETONE DERIVATIVE; PHOSPHATE; TOLUENE; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDRATION; SUZUKI MIYAURI REACTION; SYNTHESIS;

EID: 0037420996     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02501-7     Document Type: Article

References (15)

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5. For other ketone synthesis, the efficient methods using three-component coupling or organotin compounds were reported. See: (a) Ishiyama, T.; Kizaki, K.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998, 63, 4726-4731; (b) Kosugi, M.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 1423-1424; (c) Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129-6137.
6. For other ketone synthesis, the efficient methods using three-component coupling or organotin compounds were reported. See: (a) Ishiyama, T.; Kizaki, K.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998, 63, 4726-4731; (b) Kosugi, M.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 1423-1424; (c) Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129-6137.
7. For other ketone synthesis, the efficient methods using three-component coupling or organotin compounds were reported. See: (a) Ishiyama, T.; Kizaki, K.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998, 63, 4726-4731; (b) Kosugi, M.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 1423-1424; (c) Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129-6137.
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12. 4 (360 mg, 1.5 mmol) in toluene (5 mL) under nitrogen was added benzoyl chloride (141 mg, 1.0 mmol). The reaction mixture was heated at 110°C for 4 h and diluted with toluene (10 mL). The solution was washed successively with a saturated solution of sodium bicarbonate, water, and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting material was purified by column chromatography (silica gel, 1:9 ethyl acetate-hexanes) to give 2-cyanobenzophenone (145 mg, 70%) identical with authentic material purchased from Aldrich.
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