Circumventing redox chemistry: Synthesis of transition metal boryl complexes from a boryl nucleophile by decarbonylation

Journal of the American Chemical Society

Volumn 136, Issue 44, 2014, Pages 15730-15741

  Frank, René ^a   Howell, James ^a   Tirfoin, Rémi ^a   Dange, Deepak ^b   Jones, Cameron ^b   Mingos, D Michael P ^a   Aldridge, Simon ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DECARBONYLATIONS; REDOX CHEMISTRY;

CARBENE; CARBON; CARBON MONOXIDE; COBALT; LITHIUM DERIVATIVE; MANGANESE; METAL COMPLEX; NUCLEOPHILE; PYRIDINE DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; ATOM; CHEMICAL MODIFICATION; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DECOMPOSITION; DISSOCIATION; ELECTRON TRANSPORT; ELECTROPHILICITY; INFRARED SPECTROSCOPY; ISOMERIZATION; ISOTOPE LABELING; NUCLEOPHILICITY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84908626430     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja508979x     Document Type: Article

References (74)

1. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483
2. Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168
3. Fe, Ru, W: Waltz, K. M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 11358-11369
4. Mn, Fe, Re: Waltz, K. M.; He, X.; Muhoro, C. N.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11357-11358
5. Mn, Fe, Re: Waltz, K. M.; Muhoro, C. N.; Hartwig, J. F. Organometallics 1999, 18, 3383-3393
6. Männig, D.; Nöth, H. Angew. Chem., Int. Ed. 1985, 24, 878-879
7. Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179-1191
8. Wadepohl, H. Angew. Chem., Int. Ed. 1997, 36, 2441-2444
9. Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957-5026
10. Han, L. B.; Tanaka, M. Chem. Commun. 1999, 395-402
11. Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695-4712
12. Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018-11019
13. Iverson, C. N.; Smith, M. R., III J. Am. Chem. Soc. 1995, 117, 4403
14. Iverson, C. N.; Smith, M. R., III Organometallics 1996, 15, 5155-5165
15. Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137-5154
16. Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713-720
17. Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1996, 2073-2074
18. Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392-402
19. Segawa, Y.; Yamashita, M.; Nozaki, K. Science 2006, 314, 113-115
20. Segawa, Y.; Suzuki, Y.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2008, 130, 16069-16079
21. Yamashita, M.; Suzuki, Y.; Segawa, Y.; Nozaki, K. Chem. Lett. 2008, 37, 802-803
22. Segawa, Y.; Suzuki, Y.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 9600
23. Mg: Yamashita, M.; Suzuki, Y.; Segawa, Y.; Nozaki, K. J. Am. Chem. Soc. 2007, 129, 9570-9571
24. Mg, Cu, Zn: Yamashita, M.; Nozaki, K. Bull. Chem. Soc. Jpn. 2008, 81, 1377-1392
25. Al: Dettenrieder, N.; Dietrich, H. M.; Schädle, C.; Maichle-Mössmer, C.; Törnroos, K. W.; Anwander, R. Angew. Chem., Int. Ed. 2012, 51, 4461-4465
26. Al: Dettenrieder, N.; Hollfelder, C. O.; Jende, L. N.; Maichle-Mössmer, C.; Anwander, R. Organometallics 2014, 33, 1528-1531
27. Ga: Dettenrieder, N.; Schädle, C.; Maichle-Mössmer, C.; Sirsch, P.; Anwander, R. J. Am. Chem. Soc. 2014, 136, 886-889
28. Ga, In, Tl: Protchenko, A. V.; Dange, D.; Harmer, J. R.; Tang, C. Y.; Schwarz, A. D.; Kelly, M. J.; Phillips, N.; Tirfoin, R.; Birjkumar, K. H.; Jones, C.; Kaltsoyannis, N.; Mountford, P.; Aldridge, S. Nat. Chem. 2014, 6, 315-319
29. Si, Ge, Sn: Protchenko, A. V.; Birjkumar, K. H.; Dange, D.; Schwarz, A. D.; Vidovic, D.; Jones, C.; Kaltsoyannis, N.; Mountford, P.; Aldridge, S. J. Am. Chem. Soc. 2012, 134, 6500-6503
30. Pb, Cd, Hg: Protchenko, A. V.; Dange, D.; Schwarz, A. D.; Tang, C. Y.; Phillips, N.; Mountford, P.; Jones, C.; Aldridge, S. Chem. Commun. 2014, 50, 3841-3844
31. Saleh, L. M. A.; Birjkumar, K. H.; Protchenko, A. V.; Schwarz, A. D.; Aldridge, S.; Jones, C.; Kaltsoyannis, N.; Mountford, P. J. Am. Chem. Soc. 2011, 133, 3836-3839
32. Li, S.; Cheng, J.; Chen, Y.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2011, 50, 6360-6363
33. Cu: Okuno, Y.; Yamashita, M.; Nozaki, K. Eur. J. Org. Chem. 2011, 3951-3958
34. Cu: Okuno, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2011, 50, 920-923
35. Cu, Ag, Au: Segawa, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2007, 46, 6710-6713
36. Cu, Zn: Kajiwara, T.; Terabayashi, T.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2008, 47, 6606-6610
37. Ti, Hf; Terabayashi, T.; Kajiwara, T.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 14162-14163
38. -1: http://www.webelements.com/periodicity/ionisation-energy-2/ (accessed August 31, 2014).
39. Baker, R. J.; Jones, C.; Platts, J. A. Dalton Trans. 2003, 19, 3673-3674
40. Protchenko, A. V.; Saleh, L. M. A.; Vidovic, D.; Dange, D.; Jones, C.; Mountford, P.; Aldridge, S. Chem. Commun. 2010, 46, 8546-8548
41. Calderazzo, F. Angew. Chem., Int. Ed. 1977, 16, 299-311
42. Kays, D. L.; Aldridge, S. Struct. Bonding (Berlin, Ger.) 2008, 130, 29-122
43. Fe: Hartwig, J. F.; Huber, S. J. Am. Chem. Soc. 1993, 115, 4908-4909
44. Nöth, H.; Schmid, G. Allg. Prakt. Chem. 1966, 17, 610-618
45. Schmid, G. Angew. Chem., Int. Ed. 1970, 9, 819-830
46. 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
47. Braunschweig, H.; Dewhurst, R. D.; Schneider, A. Chem. Rev. 2010, 110, 3924-3957
48. Tran, B. L.; Adhikari, D.; Fan, H.; Pink, M.; Mindiola, D. J. Dalton Trans. 2010, 358-360
49. Lin, T.-P.; Peters, J. C. J. Am. Chem. Soc. 2013, 135, 15310-15313
50. Dai, C.; Stringer, G.; Corrigan, J. F.; Taylor, N. J.; Marder, T. B.; Norman, N. C. J. Organomet. Chem. 1996, 513, 273-275
51. Adams, C. J.; Baber, R. A.; Batsanov, A. S.; Bramham, G.; Charmant, J. P. H.; Haddow, M. F.; Howard, J. A. K.; Lam, W. H.; Lin, Z.; Marder, T. B.; Norman, N. C.; Orpen, A. G. Dalton Trans. 2006, 1370-1373
52. Hieber, W.; Duchatsch, H. Chem. Ber. 1965, 98, 1744-1748
53. Tasi, M.; Palyi, G. Organometallics 1985, 4, 1523-1528
54. Lavigne, F.; Maerten, E.; Alcaraz, G.; Branchadell, V.; Saffron-Merceron, N.; Baceiredo, A. Angew. Chem., Int. Ed. 2012, 51, 2489-2491
55. Krueger, C.; Goddard, R.; Claus, K. H. Z. Naturforsch., B: Chem. Sci. 1983, 38, 1431-1440
56. Mills, O. S.; Redhouse, A. D. Angew. Chem., Int. Ed. 1965, 4, 1082
57. Darensbourg, M. Y.; Darensbourg, D. J. Inorg. Chem. 1970, 9, 32-39
58. For a related (amido)manganese complex, see: Hicks, J.; Jones, C. Inorg. Chem. 2013, 52, 3900-3907
59. For terphenyl systems displaying similar structures, see: Ellison, J. J.; Power, P. P. J. Organomet. Chem. 1996, 526, 263-267
60. Zhu, J.; Lin, Z.; Marder, T. B. Inorg. Chem. 2005, 44, 9384-9390
61. Closson, R. D.; Kozikowski, J.; Coffield, T. H. J. Org. Chem. 1957, 22, 598
62. Hieber, W.; Braun, G.; Beck, W. Chem. Ber. 1960, 93, 901-908
63. King, R. B. J. Am. Chem. Soc. 1963, 85, 1918-1922
64. King, R. B.; Bisnette, M. B. J. Organomet. Chem. 1964, 2, 15-37
65. Braunschweig, H.; Kollmann, C.; Koster, M.; Englert, U.; Müller, M. Eur. J. Inorg. Chem. 1999, 2277-2281
66. Rablen, P. R.; Hartwig, J. F.; Nolan, S. P. J. Am. Chem. Soc. 1994, 116, 4121-4122
67. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520
68. Kruck, T.; Noack, M. Chem. Ber. 1964, 97, 1693-1703
69. Brodie, A. M.; Hulley, G.; Johnson, B. F. G.; Lewis, J. J. Organomet. Chem. 1970, 24, 201-203
70. Cavanaugh, M. D.; Gregg, B. T.; Chiulli, R. J.; Cutler, A. R. J. Organomet. Chem. 1997, 547, 173-182
71. Busetto, L.; Graziani, M.; Belluco, U. Inorg. Chem. 1971, 10, 78-80
72. Gallo, V.; Mastrorilli, P.; Nobile, C. F.; Braunstein, P.; Englert, U. Dalton Trans. 2006, 2342-2349
73. Sundararaman, A.; Jäkle, F. J. Organomet. Chem. 2003, 681, 134-142
74. Ruiz, J.; Lacoste, M.; Astruc, D. J. Am. Chem. Soc. 1990, 112, 5471-5483