Water as the reaction medium for multicomponent reactions based on boronic acids

Tetrahedron

Volumn 66, Issue 14, 2010, Pages 2736-2745

  Candeias, Nuno R ^a   Cal, Pedro M S D ^a   André, Vânia ^b   Duarte, M Teresa ^b   Veiros, Luís F ^b   Gois, Pedro M P ^a  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Boron; Boron heterocycles; Multicomponent reactions; Petasis reaction

Indexed keywords

AMINE; AMINO ACID DERIVATIVE; AMINOPHENOL DERIVATIVE; BORONIC ACID DERIVATIVE; CHROMENE DERIVATIVE; GLYOXAL; GLYOXYLIC ACID; HETEROCYCLIC COMPOUND; MORPHOLINE DERIVATIVE; SALICYLALDEHYDE; WATER;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENERGY; MANNICH REACTION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77649179431     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.084     Document Type: Article

References (81)

1. Zhu J., and Bienaymé H. Multicomponent Reactions (2005), Wiley-VCH, Weinheim
2. Breslow R., and Maitra U. Tetrahedron Lett. 25 (1984) 1239-1240
3. Breslow R., Maitra U., and Rideout D. Tetrahedron Lett. 24 (1983) 1901-1904
4. Rideout D.C., and Breslow R. J. Am. Chem. Soc. 102 (1980) 7816-7817
5. Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., and Sharpless K.B. Angew. Chem., Int. Ed. 44 (2005) 3275-3279
6. Jung Y.S., and Marcus R.A. J. Am. Chem. Soc. 129 (2007) 5492-5502
7. Chanda A., and Fokin V.V. Chem. Rev. 109 (2009) 725-748
8. Herrerias C.I., Yao X., Li Z., and Li C.J. Chem. Rev. 107 (2007) 2546-2562
9. Lindstrom U.M. Chem. Rev. 102 (2002) 2751-2771
10. Li C.J., and Chen L. Chem. Soc. Rev. 35 (2006) 68-82
11. Lindström U.M. Organic Reactions in Water: Principles, Strategies and Applications (2007), Blackwell., Oxford
12. Lindstrom U.M., and Andersson F. Angew. Chem., Int. Ed. 45 (2006) 548-551
13. Pirrung M.C., and Sarma K.D. Synlett (2004) 1425-1427
14. Pirrung M.C., and Sarma K.D. J. Am. Chem. Soc. 126 (2004) 444-445
15. Pirrung M.C., and Sarma K.D. Tetrahedron 61 (2005) 11456-11472
16. Pirrung M.C. Chem.-Eur. J. 12 (2006) 1312-1317
17. Pirrung M.C., Sarma K.D., and Wang J. J. Org. Chem. 73 (2008) 8723-8730
18. Candeias N.R., Branco L.C., Gois P.M.P., Afonso C.A.M., and Trindade A.F. Chem. Rev. 109 (2009) 2703-2802
19. Shapiro N., and Vigalok A. Angew. Chem., Int. Ed. 47 (2008) 2849-2852
20. Shi L.D., Niu L.H., Yao H., and Jiang H. J. Heterocycl. Chem. 46 (2009) 237-242
21. Alizadeh A., Rostamnia S., Zohreh N., and Hosseinpour R. Tetrahedron Lett. 50 (2009) 1533-1535
22. Shanthi G., and Perumal P.T. Synlett (2008) 2791-2794
23. Teimouri M.B., Abbasi T., and Mivehchi H. Tetrahedron 64 (2008) 10425-10430
24. Vasuki G., and Kumaravel K. Tetrahedron Lett. 49 (2008) 5636-5638
25. Kanizsai I., Gyonfalvi S., Szakonyi Z., Sillanpaa R., and Fulop F. Green Chem. 9 (2007) 357-360
26. Petasis N.A., and Zavialov I.A. J. Am. Chem. Soc. 119 (1997) 445-446
27. Petasis N.A., and Zavialov I.A. J. Am. Chem. Soc. 120 (1998) 11798-11799
28. Candeias N.R., Veiros L.F., Afonso C.A.M., and Gois P.M.P. Eur. J. Org. Chem. (2009) 1859-1863
29. Kaiser P.F., Churches Q.I., and Hutton C.A. Aust. J. Chem. 60 (2007) 799-810
30. McLean N.J., Tye H., and Whittaker M. Tetrahedron Lett. 45 (2004) 993-995
31. Jourdan H., Gouhier G., Van Hijfte L., Angibaud P., and Piettre S.R. Tetrahedron Lett. 46 (2005) 8027-8031
32. Prakash G.K.S., Mandal M., Schweizer S., Petasis N.A., and Olah G.A. Org. Lett. 2 (2000) 3173-3176
33. Wang Q., and Finn M.G. Org. Lett. 2 (2000) 4063-4065
34. Petasis N.A., and Butkevich A.N. J. Organomet. Chem. 694 (2009) 1747-1753
35. Portlock D.E., Naskar D., West L., and Li M. Tetrahedron Lett. 43 (2002) 6845-6847
36. Berrée F., Debache A., Marsac Y., Collet B., Girard-Le Bleiz P., and Carboni B. Tetrahedron 62 (2006) 4027-4037
37. Regnier T., Berree F., Lavastre O., and Carboni B. Green Chem. 9 (2007) 125-126
38. Selected examples:
39. Barba V., Rodríguez A., Ochoa M.E., Santillan R., and Farfán N. Inorg. Chim Acta 357 (2004) 2593-2601
40. Abreu A., Alas S.J., Beltrán H.I., Santillan R., and Farfán N. J. Organomet. Chem. 691 (2006) 337-348
41. Braun M., Schlecht S.M., Engelmann M., and Frank W. Eur. J. Org. Chem. (2008) 5221-5225
42. Kaiser P.F., White J.M., and Hutton C.A. J. Am. Chem. Soc. 130 (2008) 16450-16451
43. Christinat N., Croisier E., Scopelliti R., Cascella M., Röthlisberger U., and Severin K. Eur. J. Inorg. Chem. (2007) 5177-5181
44. Christinat N., Scopelliti R., and Severin K. J. Org. Chem. 72 (2007) 2192-2200
45. Christinat N., Scopelliti R., and Severin K. Angew. Chem., Int. Ed. 47 (2008) 1848-1852
46. Farfán N., Höpfl H., Barba V., Ochoa M.E., Santillan R., Gómez E., and Gutiérrez A. J. Organomet. Chem. 581 (1999) 70-81
47. Beltrán H.I., Zamudio-Rivera L.S., Mancilla T., Santillan R., and Farfán N. J. Organomet. Chem 657 (2002) 194-204
48. Parr R.G., and Yang W. Density Functional Theory of Atoms and Molecules (1989), Oxford University Press, New York
49. Wiberg K.B. Tetrahedron 24 (1968) 1083-1096
50. Wiberg indices are electronic parameters related to the electron density between atoms. They can be obtained from a Natural Population Analysis and provide an indication of the bond strength.
51. Carpenter J.E., and Weinhold F. J. Mol. Struct. (Theochem) 169 (1988) 41-62
52. Carpenter, J.E. PhD Thesis, University of Wisconsin (Madison WI), 1987.
53. Foster J.P., and Weinhold F. J. Am. Chem. Soc. 102 (1980) 7211-7118
54. Reed A.E., and Weinhold F. J. Chem. Phys. 78 (1983) 4066-4073
55. Reed A.E., and Weinhold F. J. Chem. Phys. 78 (1985) 1736-1740
56. Reed A.E., Weinstock R.B., and Weinhold F. J. Chem. Phys. 83 (1985) 735-746
57. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (1988) 899-926
58. Weinhold F., and Carpenter J.E. The Structure of Small Molecules and Ions (1988), Plenum, New York p. 227
59. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford CT
60. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), John Wiley & Sons, New York
61. Perdew J.P., Burke K., and Ernzerhof M. Phys. Rev. Lett. 78 (1997) 1396
62. Perdew J.P. Phys. Rev. B 33 (1986) 8822-8824
63. Ditchfield R., Hehre W.J., and Pople J.A. J. Chem. Phys. 54 (1971) 724-728
64. Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257-2261
65. Hariharan P.C., and Pople J.A. Mol. Phys. 27 (1974) 209-214
66. Gordon M.S. Chem. Phys. Lett. 76 (1980) 163-168
67. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213-222
68. Peng C.Y., Ayala P.Y., Schlegel H.B., and Frisch M.J. J. Comp. Chem. 17 (1996) 49-56
69. Peng C., and Schlegel H.B. Israel J. Chem. 33 (1993) 449-454
70. McClean A.D., and Chandler G.S. J. Chem. Phys. 72 (1980) 5639-5648
71. Krishnan R., Binkley J.S., Seeger R., and Pople J.A. J. Chem. Phys. 72 (1980) 650-654
72. Wachters A.J.H. J. Chem. Phys. 52 (1970) 1033-1036
73. Hay P.J. J. Chem. Phys. 66 (1977) 4377-4384
74. Raghavachari K., and Trucks G.W. J. Chem. Phys. 91 (1989) 1062-1065
75. Binning R.C., and Curtiss L.A. J. Comput. Chem. 103 (1995) 6104-6113
76. McGrath M.P., and Radom L. J. Chem. Phys. 94 (1991) 511-516
77. Cancès E., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032-3041
78. Cossi M., Barone V., Mennucci B., and Tomasi J. Chem. Phys. Lett. 286 (1998) 253-260
79. Mennucci B., and Tomasi J. J. Chem. Phys. 106 (1997) 5151-5158
80. Tomasi J., Mennucci B., and Cammi R. Chem. Rev. 105 (2005) 2999-3093
81. Cossi M., Scalmani G., Rega N., and Barone V. J. Chem. Phys. 117 (2002) 43-54