Preparation of cobalt-containing bulky monodentate phosphines with electron-withdrawing/donating substituents on bridged arylethynyl and their applications in Suzuki coupling reactions

Tetrahedron

Volumn 64, Issue 27, 2008, Pages 6221-6229

  Shiu, Bo Yuan ^a   Huang, Po Cheng ^a   Huang, Yi Luen ^a   Hong, Fung E ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

DFT methods; Electron withdrawing substituent; ortho Metalation; Phosphine ligand; Suzuki Miyaura cross coupling reaction; Transmetalation

Indexed keywords

COBALT; MONODENTATE PHOSPHINE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; ELECTRON TRANSPORT; PRIORITY JOURNAL; SUZUKI REACTION; SYNTHESIS;

EID: 44349129697     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.117     Document Type: Article

References (80)

1. Hassan J., Sévignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
2. In: Cornils B., and Herrmann W.A. (Eds). Applied Homogeneous Catalysis with Organometallic Compounds Vols. 1 and 2 (1996), VCH, New York, NY
3. Parshall G.W., and Ittel S.D. Homogeneous Catalysis. 2nd ed. (1992;), John Wiley and Sons, New York, NY Chapter 8
4. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
5. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176
6. Espinet P., and Echavarren A.M. Angew. Chem., Int. Ed. 43 (2004) 4704
7. Goossen L.J., Koley D., Hermann H., and Thiel W. Organometallics 24 (2005) 2398
8. Barder T.E., Walker S.D., Martinelli J.R., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4685
9. Kozuch S., Amatore C., Jutand A., and Shaik S. Organometallics 24 (2005) 2319
10. Barder T.E. J. Am. Chem. Soc. 128 (2006) 898
11. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-coupling Reactions (1998), Wiley-VCH, Weinheim, Germany
12. Casado A.L., and Espinet P. Organometallics 17 (1998) 954
13. Barrios-Landeros F., and Hartwig J.F. J. Am. Chem. Soc. 127 (2005) 6944
14. Gillie A., and Stille J.K. J. Am. Chem. Soc. 102 (1980) 4933
15. Sundermann A., Uzan O., and Martin J.M.L. Chem.-Eur. J. 7 (2001) 1703
16. Ananikov V.P., Musaev D.G., and Morokuma K. J. Am. Chem. Soc. 124 (2002) 2839
17. Senn H.M., and Ziegler T. Organometallics 23 (2004) 2980
18. Zuidema E., van Leeuwen P.W.N.M., and Bo C. Organometallics 24 (2005) 3703
19. Aliprantis A.O., and Canary J.W. J. Am. Chem. Soc. 116 (1994) 6985
20. Nishihara Y., Onodera H., and Osakada K. Chem. Commun. (2004) 192
21. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029
22. Andersen N.G., and Keay B.A. Chem. Rev. 101 (2001) 997
23. Bessel C.A., Aggarwal P., Marschilok A.C., and Takeuchi K.J. Chem. Rev. 101 (2001) 1031
24. Walker S.D., Barder T.E., Martinelli J.R., and Buchwald S.L. Angew. Chem., Int. Ed. 43 (2004) 1871
25. Hawtig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046
26. Mann G., and Hartwig J.F. J. Am. Chem. Soc. 118 (1996) 13109
27. Kataoka N., Shelby Q., Stambuli J.P., and Hartwig J.F. J. Org. Chem. 67 (2002) 5553
28. Littke A.F., Dai C., and Fu G.C. J. Am. Chem. Soc. 122 (2000) 4020
29. Planas J.G., and Gladysz J.A. Inorg. Chem. 41 (2002) 6947
30. Hu Q.-S., Lu Y., Tang Z.-Y., and Yu H.-B. J. Am. Chem. Soc. 125 (2003) 2856
31. Pickett T.E., Roca F.X., and Richards C.J. J. Org. Chem. 68 (2003) 2592
32. Tang Z.-Y., Lu Y., and Hu Q.-S. Org. Lett. 5 (2003) 297
33. For general reviews, see:
34. Delacroix O., and Gladysz J.A. Chem. Commun. (2003) 665
35. Salzer A. Coord. Chem. Rev. 242 (2003) 59
36. Jesen J.F., and Johannsen M. Org. Lett. 5 (2003) 3025
37. See Refs. 8g,h,k,l.
38. Hong F.-E., Chang Y.-C., Chang R.-E., Chen S.-C., and Ko B.-T. Organometallics 21 (2002) 961
39. Chang Y.-C., and Hong F.-E. Organometallics 24 (2005) 5686
40. Hong F.-E., Ho Y.-J., Chang Y.-C., and Huang Y.-L. J. Organomet. Chem. 690 (2005) 1249
41. Chang C.-P., Huang Y.-L., and Hong F.-E. Tetrahedron 61 (2005) 3835
42. Hong F.-E., Chang Y.-C., Chang C.-P., and Huang Y.-L. Dalton Trans. (2004) 157
43. Hong F.-E., Ho Y.-J., Chang Y.-C., and Lai Y.-C. Tetrahedron 60 (2004) 2639
44. Hong F.-E., Chang C.-P., and Chang Y.-C. Dalton Trans. (2003) 3892
45. Hong F.-E., Lai Y.-C., Ho Y.-J., and Chang Y.-C. J. Organomet. Chem. 688 (2003) 161
46. Lee J.-C., Wang M.-G., and Hong F.-E. Eur. J. Inorg. Chem. (2005) 5011
47. Buchwald S.L., and Zim D. Org. Lett. 5 (2003) 2413
48. O'Connor T.J., and Patel H.A. Can. J. Chem. 49 (1971) 2706
49. Gan Y.-H., Lee J.-C., and Hong F.-E. Polyhedron 25 (2006) 3555
50. Bedford R.B., Hazelwood S.L., Horton P.N., and Hursthouse M.B. Dalton Trans. (2003) 4164
51. Dewar M.J.S. Bull. Soc. Chim. Fr. 18 (1951) C71
52. Chatt J., and Duncanson L.A. J. Chem. Soc. (1953) 2939
53. Goldman E.R., Medintz I.L., Whitley J.L., Hayhurst A., Clapp A.R., Uyeda H.T., Deschamps J.R., Lassman M.E., and Mattoussi H. J. Am. Chem. Soc. 127 (2005) 6744
54. Braga A.A.C., Morgon N.H., Ujaque G., and Maseras F. J. Am. Chem. Soc. 127 (2005) 9298
55. Yin J., Rainka M.P., Zhang X.X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 1162
56. Bedford R.B., and Cazin C.S. Chem. Commun. (2001) 1540
57. Stambuli J.P., Bühl M., and Hartwig J.F. J. Am. Chem. Soc. 124 (2002) 9346
58. Beare N.A., and Hartwig J.F. J. Org. Chem. 67 (2002) 541
59. Stambuli J.P., Stauffer S.R., Shaughnessy K.H., and Hartwig J.F. J. Am. Chem. Soc. 123 (2001) 2677
60. Netherton M.R., and Fu G.C. Org. Lett. 3 (2001) 4295
61. Aranoys A., Old D.W., Kiyomory A., Wolfe J.P., Sadighi J.P., and Buchwald S.L. J. Am. Chem. Soc. 121 (1999) 4369
62. Miyaura N., Yamada K., Suginome H., and Suzuki A. J. Am. Chem. Soc. 107 (1985) 972
63. Grasa G.A., Hillier A.C., and Nolan S.P. Org. Lett. 3 (2001) 1077
64. Dubbaka S.R., and Vogel P. Org. Lett. 6 (2004) 95
65. Pople J.A. Angew. Chem., Int. Ed. 38 (1999) 1894
66. Hehre W.J., Radom L., Schleyer P.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley-Interscience, New York, NY
67. Koch W., and Holthausen M.C. A Chemist's Guide to Density Functional Theory (2000), Wiley-VCH, Weinheim
68. Ziegler T. Chem. Rev. 91 (1991) 651
69. Davidson E.R. Chem. Rev. 100 (2002) 351
70. Sheldrick G.M. SHELXTL PLUS User's Manual. Revision 4.1 (1991), Nicolet XRD Corporation, Madison, Wisconsin, USA
71. The hydrogen atoms were ride on carbons or oxygens in their idealized positions and held fixed with the C-H distances of 0.96 Å.
72. 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., Bakken V., 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
73. Becke A.D. J. Chem. Phys. 98 (1993) 5648
74. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
75. Dunning Jr. T.H., and Hay P.J. Modern Theoretical Chemistry (1976), Plenum, New York, NY p 1
76. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 299
77. Reed A.E., Weinstock R.B., and Weinhold F. J. Chem. Phys. 83 (1985) 735
78. Glendening E.D., Badenhoop J.K., Reed A.E., Carpenter J.E., Bohmann J.A., Morales C.M., and Weinhold F. NBO 5.0 (2001), Theoretical Chemistry Institute, University of Wisconsin, Madison, WI
79. Seeger R., and Pople J.A. J. Chem. Phys. 66 (1977) 3045
80. Bauernschmitt R., and Ahlrichs R. J. Chem. Phys. 104 (1996) 9047