Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 3057-3060

  Bumagin, Nikolay A ^a   Korolev, Dmitriy N ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BENZOPHENONE DERIVATIVE; BENZYL CHLORIDE; BICARBONATE; BORANE DERIVATIVE; BORATE SODIUM; BORONIC ACID DERIVATIVE; CHLORIDE; KETONE DERIVATIVE; LIGAND; PALLADIUM;

ACYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; SYNTHESIS;

EID: 0033537808     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00364-0     Document Type: Article

References (22)

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5. For reviews, see (e). Suzuki, A. Pure Appl.Chem. 1985, 57, 1749.
6. (f). Suzuki, A. ibid. 1991, 63, 419.
7. (g). Miyaura, N.; Suzuki, A. Chem.Rev. 1995, 95, 2457.
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9. (b). Bumagin, N.A.; Bykov, V.V.; Beletskaya, I.P. Dokl.Akad.Nauk. 1990, 315, 1133.
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11. (d). Bumagin, N.A.; Bykov, V.V. Tetrahedron. 1997, 53, 14437.
12. See also (e). Wallow, T.I.; Novak, B.M. J.Org.Chem. 1994, 59, 5034.
13. (f). Campi, E.M.; Jackson, W.R.; Marcuccio, S.M.; Naesland, C.G.M. J.Chem.Soc., Chem.Commun. 1994, 2395.
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15. (a). Bykov, V.V.; Kir'yanov, A.A.; Bumagin, N.A.; Beletskaya, I.P. Izvest.Akad.Nauk SSSR, Ser.Khim. 1996, 1582.
16. See also (b). Moreno-Manas, M.; Pajuelo, F.; Pleixats, R. J.Org.Chem. 1995, 60, 6296.
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18. 4 (0.25 mmole) in acetone (9ml) under argon. The reaction mixture was stirred at 20°C for the period indicated in the Table 1. The products were isolated by TLC over silica gel.
19. 2O (1 ml) and 6 ml of acetone under argon. The reaction mixture was stirred at 20°C for the period indicated in the Table 2. The products were isolated by TLC over silica gel.
20. 6): 8.57(dd, 1 H, J=1 Hz, J=5 Hz, thiophene ring), 8.48(dd, 2 H, J=1.5 Hz, J=7 Hz, o-H, Ph), 8.31(dd, 1 H, J=1 Hz, J=3.5 Hz, thiophene ring), 8.26(t, 1 H, J=4, thiophene ring), 8.12(t, 2 H, J=7.5, m-H, Ph), 7.86(dd, 1 H, J=3.5 Hz, J=5 Hz, p-H, Ph).
21. 6): 8.2(m, 3 H), 7.8(m, 1 H), 7.65(m, 3 H).
22. 6): 10.09(br s, 1 H, CHO), 8.62(br s, 1 H, thiophene ring), 8.38(br s, 1 H, thiophene ring), 7.91(d, 2 H, J=7 Hz, o-H, Ph), 7.70(t, 1 H, J=7.5 Hz, p-H, Ph), 7.59(t, 2 H, J=7.5 Hz, m-H, Ph).