Ditopic ambiphilicity of an anionic dimetalloborylene complex

Journal of the American Chemical Society

Volumn 135, Issue 6, 2013, Pages 2313-2320

  Braunschweig, Holger ^a   Damme, Alexander ^a   Dewhurst, Rian D ^a   Kramer, Thomas ^a   Östreicher, Sebastian ^a   Radacki, Krzysztof ^a   Vargas, Alfredo ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BORON ATOM; ELECTROPHILES; ELECTROPHILICITY; HEAVIER HALIDES; LEWIS BASE; MAIN GROUP; METAL CHLORIDES; METHYL IODIDE; NUCLEOPHILIC BEHAVIORS; NUCLEOPHILIC SUBSTITUTIONS;

CHLORINE COMPOUNDS; MANGANESE; METAL HALIDES; NEGATIVE IONS; TRANSITION METALS;

BORON;

ANION; ANIONIC DIMETALLOBORYLENE COMPLEX; BORON; BORYL LITHIUM; CHLORIDE; ELECTROPHILE; GOLD; HALIDE; LEWIS BASE; LITHIUM DERIVATIVE; MANGANESE; METAL COMPLEX; METHYL IODIDE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; DITOPICITY; ELECTROPHILICITY; NUCLEOPHILICITY; PHASE TRANSITION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

ANIONS; BORON COMPOUNDS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MANGANESE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 84873686583     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja310895w     Document Type: Article

References (71)

1. Wagner, M.; Hommes, N. J. R. V.; Nöth, H.; Schleyer, P. v. R. Inorg. Chem. 1995, 34, 607-614
2. Kirmse, W. Carbene Chemistry, 2 nd ed.; Academic Press: New York, 1971.
3. Wentrup, C. Reactive Molecules; Wiley: New York, 1984.
4. Moss, R. A.; Jones, M., Jr. Carbenes, Vol. I; Wiley: New York, 1973.
5. Moss, R. A.; Jones, M., Jr. Carbenes, Vol. II; Wiley: New York, 1975.
6. Dekker, M. Carbene Chemistry; New York, 2005.
7. Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91
8. Irvine, G. J.; Lesley, M. J. G.; Marder, T. B.; Norman, N. C.; Rice, C. R.; Robins, E. G.; Roper, W. R.; Whittell, G. R.; Wright, L. J. Chem. Rev. 1998, 98, 2685-2722
9. Marder, T. B.; Norman, N. C. Top. Catal. 1998, 5, 63-73
10. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890-931
11. Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864-873
12. Braunschweig, H.; Dewhurst, R. D.; Schneider, A. Chem. Rev. 2010, 110, 3924-3957
13. Entwistle, C. D.; Marder, T. B. Angew. Chem., Int. Ed. 2002, 41, 2927-2931
14. Entwistle, C. D.; Marder, T. B. Chem. Mater. 2004, 16, 4574-4585
15. Braunschweig, H.; Rais, D. Angew. Chem., Int. Ed. 2005, 44, 7826-7828
16. Jaekle, F. J. Inorg. Organomet. P. 2005, 15, 293-307
17. Hudson, Z. M.; Wang, S. N. Dalton Trans. 2011, 40, 7805-7816
18. Hudson, Z. M.; Wang, S. N. Acc. Chem. Res. 2009, 42, 1584-1596
19. Cheng, F.; Jaekle, F. Polym. Chem. 2011, 10, 2122-2132
20. Mannig, D.; Nöth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878-879
21. Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179-1191
22. Wadepohl, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2441-2444
23. Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957-5026
24. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392-402
25. Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695-4712
26. Cui, C. Z.; Bonder, E. M.; Qin, Y.; Jakle, F. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 2438-2445
27. Chen, P.; Jäkle, F. J. Am. Chem. Soc. 2011, 133, 20142-20145
28. Chen, P.; Lalancette, R. A.; Jäkle, F. J. Am. Chem. Soc. 2011, 133, 8802-8805
29. Kuhtz, H.; Cheng, F.; Schwedler, S.; Böhling, L.; Brockhinke, A.; Weber, L.; Parab, K.; Jäkle, F. ACS Macro Lett. 2012, 1, 555-559
30. Qin, Y.; Shipman, P. O.; Jakle, F. Macromol. Rapid Commun. 2012, 33, 562-567
31. Brotherton, R. J. Progress In Boron Cemistry, Vol. 1; Pergamon: New York, 1964.
32. Weber, L.; Schnieder, M.; Lonnecke, P. J. Chem. Soc., Dalton Trans. 2001, 3459-3464
33. Marder, T. B. Product Subclass 3: Diborane(4) Compounds; Science of Synthesis; Georg Thieme Verlag: Stuttgart-New York, 2005; Vol. 6.
34. Segawa, Y.; Yamashita, M.; Nozaki, K. Science 2006, 314, 113-115
35. Braunschweig, H. Angew. Chem., Int. Ed. 2007, 46 (12) 1946-1948
36. Bauer, J.; Braunschweig, H.; Dewhurst, R. D. Chem. Rev. 2012, 112, 4329-4346
37. Braunschweig, H.; Chiu, C. W.; Radacki, K.; Kupfer, T. Angew. Chem., Int. Ed. 2010, 49, 2041-2044
38. Braunschweig, H.; Chiu, C.-W.; Kupfer, T.; Radacki, K. Inorg. Chem. 2011, 50, 4247-4249
39. Monot, J.; Solovyev, A.; Bonin-Dubarle, H.; Derat, E.; Curran, D. P.; Robert, M.; Fensterbank, L.; Malacria, M.; Lacote, E. Angew. Chem., Int. Ed. 2010, 49, 9166-9169
40. Braunschweig, H.; Burzler, M.; Dewhurst, R. D.; Radacki, K. Angew. Chem., Int. Ed. 2008, 47, 5650-5653
41. Segawa, Y.; Suzuki, Y.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2008, 130, 16069-16079
42. Segawa, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2007, 46, 6710-6713
43. Li, S. H.; Cheng, J. H.; Chen, Y. H.; Nishiura, M.; Hou, Z. M. Angew. Chem., Int. Ed. 2011, 50, 6360-6363
44. Hayashi, Y.; Segawa, Y.; Yamashita, M.; Nozaki, K. Chem. Commun. 2011, 47, 5888-5890
45. Dettenrieder, N.; Dietrich, H. M.; Schadle, C.; Maichle-Mossmer, C.; Tornroos, K. W.; Anwander, R. Angew. Chem., Int. Ed. 2012, 51, 4461-4465
46. Braunschweig, H.; Brenner, P.; Dewhurst, R. D.; Kaupp, M.; Müller, R.; Ostreicher, S. Angew. Chem., Int. Ed. 2009, 48, 9735-9738
47. Braunschweig, H.; Kraft, K.; Ostreicher, S.; Radacki, K.; Seeler, F. Chem.-Eur. J. 2010, 16, 10635-10637
48. Duffy, D. N.; Nicholson, B. K. J. Organomet. Chem. 1979, 164, 227-234
49. Both the Gaussian03 (http://www.gaussian.com/) and ADF (http://www.scm.com) suites of programmes were used for the calculations. Spin restricted calculations were performed by constraining the projection of the total electronic spin along a reference axis to zero. The zeroth-order regular approximation (ZORA) was employed for complexes containing 4d and 5d metals. Frequency calculations were conducted to determine if each stationary point corresponds to a minimum. The Jmol program (http://www.jmol.org/) and the Graphical User Interface (ADF-GUI, a part of the ADF package) were used for vizualisation purposes.
50. Braunschweig, H.; Kraft, K.; Kupfer, T.; Radacki, K.; Seeler, F. Angew. Chem., Int. Ed. 2008, 47, 4931
51. Bauer, J.; Braunschweig, H.; Dewhurst, R. D.; Kraft, K.; Radacki, K. Chem.-Eur. J. 2012, 18, 2327
52. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
53. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297
54. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623
55. Chong, D. P. Mol. Phys. 2005, 103, 749
56. Chong, D. P.; van Lenthe, E.; van Gisbergen, S. J. A.; Baerends, E. J. J. Comput. Chem. 2004, 25, 1030
57. van Lenthe, E.; Baerends, E. J. J. Comput. Chem. 2003, 24, 1142
58. Raffenetti, R. C. J. Chem. Phys. 1973, 59, 5936
59. Weinhold, F.; Landis, C. R. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: Cambridge, U.K., 2005.
60. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899
61. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639
62. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
63. Wachters, A. J. H. J. Chem. Phys. 1970, 52, 1033
64. Hay, P. J. J. Chem. Phys. 1977, 66, 4377
65. Raghavachari, K.; Trucks, G. W. J. Chem. Phys. 1989, 91, 1062
66. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294
67. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265
68. Bickelhaupt, F. M.; Baerends, E. J. Kohn-Sham Density Functional Theory: Predicting and Understanding Chemistry. In Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; Wiley-VCH: New York, 2000.
69. te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Fonseca Guerra, C.; van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931
70. Morokuma, K. Acc. Chem. Res. 1977, 10, 294
71. Ziegler, T.; Rauk, A.; Baerends, E. J. Theor. Chim. Acta 1977, 43, 261