Syntheses and characterization of new vinyl-borylene complexes by the hydroboration of alkynes with [(μ3-BH)(Cp*RuCO) 2(μ-CO)Fe(CO)3]

Chemistry - A European Journal

Volumn 19, Issue 7, 2013, Pages 2337-2343

  Bose, Shubhankar Kumar ^a   Roy, Dipak Kumar ^a   Shankhari, Pritam ^a   Yuvaraj, K ^a   Mondal, Bijan ^a   Sikder, Amrita ^a   Ghosh, Sundargopal ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

alkynes; boron; borylene; hydroboration; photolysis; ruthenium

Indexed keywords

2-BUTYNE; ALKYNES; BORYLENE COMPLEXES; BORYLENES; CRYSTALLOGRAPHIC ANALYSIS; DENSITY FUNCTIONAL THEORY METHODS; HYDROBORATION; INTERNAL ALKYNES; NMR CHEMICAL SHIFTS; PHENYLACETYLENES; PLAUSIBLE MECHANISMS; ROOM TEMPERATURE; STRUCTURAL TYPE;

AROMATIC HYDROCARBONS; BORON; DENSITY FUNCTIONAL THEORY; IRON COMPOUNDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOLYSIS; RUTHENIUM;

ACETYLENE;

EID: 84873375879     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203627     Document Type: Article

References (82)

1. H. Braunschweig, Angew. Chem. 1998, 110, 1882-1898
2. Angew. Chem. Int. Ed. 1998, 37, 1786-1801
3. H. Braunschweig, M. Colling, J. Organomet. Chem. 2000, 614, 18-26
4. H. Braunschweig, M. Colling, Coord. Chem. Rev. 2001, 223, 1-51
5. H. Braunschweig, in Inorganic Chemical Highlights (Eds.:, G. Mayer, D. Naumann, L. Wesemann,), Wiley-VCH, Weinheim, 2001, pp. 213-218
6. S. Aldridge, D. L. Coombs, Coord. Chem. Rev. 2004, 248, 535-559
7. D. Vidovic, G. A. Pierce, S. Aldridge, Chem. Commun. 2009, 1157-1171
8. H. Braunschweig, R. D. Dewhurst, A. Schneider, Chem. Rev. 2010, 110, 3924-3957, and references therein.
9. H. Braunschweig, C. Kollann, D. Rais, Angew. Chem. 2006, 118, 5380-5400
10. Angew. Chem. Int. Ed. 2006, 45, 5254-5274
11. H. Braunschweig, T. Wagner, Angew. Chem. 1995, 107, 904-905
12. Angew. Chem. Int. Ed. Engl. 1995, 34, 825-826.
13. H. Braunschweig, C. Kollann, U. Englert, Angew. Chem. 1998, 110, 3355-3357
14. Angew. Chem. Int. Ed. 1998, 37, 3179-3180
15. A. H. Cowley, V. Lomel, A. Voigt, J. Am. Chem. Soc. 1998, 120, 6401-6402.
16. H. Braunschweig, R. D. Dewhurst, Chem. Today 2009, 27, 40-42.
17. R. Wilczynski, L. G. Sneddon, J. Am. Chem. Soc. 1980, 102, 2857-2858
18. R. Wilczynski, L. G. Sneddon, Inorg. Chem. 1981, 20, 3955-3962
19. R. Wilczynski, L. G. Sneddon, Inorg. Chem. 1982, 21, 506-514.
20. Boron Hydride Chemistry (Ed.:, E. L. Muetterties,), Academic Press, New York, 1975
21. R. N. Grimes, Carboranes, 2 nd ed., Academic Press, New York, 2011.
22. H. Braunschweig, T. Herbst, D. Rais, S. Ghosh, T. Kupfer, K. Radacki, A. G. Crawford, R. M. Ward, T. B. Marder, I. Fernández, G. Frenking, J. Am. Chem. Soc. 2009, 131, 8989-8999
23. H. Braunschweig, Q. Ye, K. Radacki, A. Damme, Angew. Chem. 2012, 124, 7959-7962
24. Angew. Chem. Int. Ed. 2012, 51, 7839-7842.
25. K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191
26. I. Beletskaya, A. Pelter, Tetrahedron 1997, 53, 4957-5026
27. C. M. Crudden, D. Edwards, Eur. J. Org. Chem. 2003, 4695-4712
28. C. M. Vogels, S. A. Westcott, Curr. Org. Chem. 2005, 9, 687-699
29. A. M. Carroll, T. P. O'Sullivan, P. J. Guiry, Adv. Synth. Catal. 2005, 347, 609-631.
30. H. C. Brown, B. C. S. Rao, J. Org. Chem. 1957, 22, 1136-1137
31. H. C. Brown, B. C. S. Rao, J. Org. Chem. 1957, 22, 1137-1138
32. H. C. Brown, Hydroboration, Wiley-Interscience, New York, 1962
33. H. C. Brown, Organic Synthesis via Boranes, Wiley-Interscience, New York, 1975
34. G. M. L. Cragg, Organoboranes in Organic Synthesis, Marcel Dekker, New York, 1973
35. Boronic Acids-Preparation and Applications in Organic Synthesis Medicine and Materials, 2 nd ed., (Ed.: D. G. Hall,), Wiley-VCH, Weinheim, 2011.
36. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
37. H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1975, 97, 5249-5255
38. D. Männig, H. Nöth, Angew. Chem. 1985, 97, 854-855
39. Angew. Chem. Int. Ed. Engl. 1985, 24, 878-879
40. J. D. Hewes, C. W. Kreimendahl, T. B. Marder, M. F. Hawthorne, J. Am. Chem. Soc. 1984, 106, 5757-5759.
41. D. L. Coombs, S. Aldridge, C. Jones, D. J. Willock, J. Am. Chem. Soc. 2003, 125, 6356-6357
42. D. L. Coombs, S. Aldridge, A. Rossin, C. Jones, D. J. Willock, Organometallics 2004, 23, 2911-2926
43. D. L. Coombs, S. Aldridge, C. Jones, Chem. Commun. 2002, 856-857.
44. G. Alcaraz, U. Helmstedt, E. Clot, L. Vendier, S. Sabo-Etienne, J. Am. Chem. Soc. 2008, 130, 12878-12879.
45. H. Braunschweig, M. Burzler, T. Kupfer, K. Radacki, F. Seeler, Angew. Chem. 2007, 119, 7932-7934
46. Angew. Chem. Int. Ed. 2007, 46, 7785-7787
47. H. Braunschweig, Q. Ye, K. Radacki, Chem. Commun. 2012, 48, 2701-2703.
48. K. Geetharani, S. K. Bose, B. Varghes, S. Ghosh, Chem. Eur. J. 2010, 16, 11357-11366
49. K. Geetharani, S. K. Bose, S. Sahoo, S. Ghosh, Angew. Chem. 2011, 123, 3994-3997
50. Angew. Chem. Int. Ed. 2011, 50, 3908-3911
51. S. Ghosh, T. P. Fehlner, B. C. Noll, Chem. Commun. 2005, 3080-3082.
52. K. Geetharani, V. Ramkumar, S. Ghosh, Organometallics 2012, 31, 6381-6387.
53. H. Amt, W. Kliegel, S. J. Rettig, J. Trotter, Can. J. Chem. 1990, 68, 1791-1796.
54. G. A. Pierce, D. Vidovic, D. L. Kays, N. D. Coombs, A. L. Thompson, D. J. Willock, E. D. Jemmis, S. De, S. Aldridge, Organometallics 2009, 28, 2947-2960
55. D. A. Addy, N. Phillips, G. A. Pierce, D. Vidovic, T. Krämer, D. Mallick, E. D. Jemmis, G. Reid, S. Aldridge, Organometallics 2012, 31, 1092-1102.
56. D. Vidovic, S. Aldridge, Angew. Chem. 2009, 121, 3723-3726
57. Angew. Chem. Int. Ed. 2009, 48, 3669-3672
58. D. Vidovic, G. A. Pierce, N. D. Coombs, D. L. Kays, A. L. Thompson, A. Stasch, S. Aldridge, Main Group Chem. 2010, 9, 57-65.
59. C. M. Crudden, Y. B. Hleba, A. C. Chen, J. Am. Chem. Soc. 2004, 126, 9200-9201
60. J. J. J. Juliette, D. Rutherford, I. T. Horváth, J. A. Gladysz, J. Am. Chem. Soc. 1999, 121, 2696-2704
61. Y. Yamamoto, R. Fujikawa, T. Umemoto, N. Miyaura, Tetrahedron 2004, 60, 10695-10700.
62. C. Gunanathan, M. Hölscher, F. Pan, W. Leitner, J. Am. Chem. Soc. 2012, 134, 14349-14352.
63. H. Yan, A. M. Beatty, T. P. Fehlner, J. Am. Chem. Soc. 2003, 125, 16367-16382.
64. L. G. Sneddon, Pure Appl. Chem. 1987, 59, 837-846.
65. C. P. Casey, P. J. Fagan, J. Am. Chem. Soc. 1982, 104, 4950-4951.
66. C. P. Casey, M. W. Meszaros, P. J. Fagan, R. K. Bly, S. R. Marder, E. A. Austin, J. Am. Chem. Soc. 1986, 108, 4043-4053.
67. G. E. Ryschkewitsch, K. C. Nainan, Inorg. Synth. 1974, 15, 113-114.
68. SIR92, Altornare, A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, J. Appl. Crystallogr. 1993, 26, 343-350.
69. SHELXS-97, G. M. Sheldrick, University of Göttingen (Germany), 1997
70. SHELXL-97, G. M. Sheldrick, University of Göttingen (Germany), 1997.
71. A. Sorkin, D. G. Truhlar, E. A. Amin, J. Chem. Theory Comput. 2009, 5, 1254-1265.
72. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652
73. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100.
74. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
75. M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta. 1993, 85, 441-450.
76. Gaussian 09, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.
77. G. Schreckenbach, T. J. Ziegler, J. Phys. Chem. 1995, 99, 606-611.
78. G. Schreckenbach, T. J. Ziegler, Int. J. Quantum Chem. 1997, 61, 899-918.
79. G. Schreckenbach, T. J. Ziegler, Int. J. Quantum Chem. 1996, 60, 753-766.
80. S. K. Wolff, T. J. Ziegler, J. Chem. Phys. 1998, 109, 895-905.
81. S. K. Wolff, T. J. Ziegler, E. van Lethe, E. J. Baerends, J. Chem. Phys. 1999, 110, 7689-7698.
82. T. P. Onak, H. L. Landesman, R. E. Williams, I. Shapiro, J. Phys. Chem. 1959, 63, 1533-1535.