The reactivities of iminoboranes with carbenes: BN isosteres of carbene-alkyne adducts

Angewandte Chemie - International Edition

Volumn 54, Issue 5, 2015, Pages 1662-1665

  Braunschweig, Holger ^a   Ewing, William C ^a   Geetharani, K ^a   Schäfer, Marius ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b NONE

Author keywords

Boron; Carbenes; Iminoborane adducts; Rearrangement

Indexed keywords

BORON; CYCLIZATION; SYNTHESIS (CHEMICAL); TEMPERATURE;

CARBENES; IMINOBORANE; INTRAMOLECULAR CYCLIZATIONS; LEWIS ACID-BASE; LOW TEMPERATURES; N-HETEROCYCLIC CARBENES; REARRANGEMENT; ROOM TEMPERATURE;

ORGANIC COMPOUNDS;

EID: 85027925197     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409699     Document Type: Article

References (62)

1. A. J. Arduengo, R. L. Harlow, M. J. Kline, J. Am. Chem. Soc. 1991, 113, 361-363.
2. For reviews and mini-reviews on the uses of stable carbenes see: a) C. D. Martin, M. Soleilhavoup, G. Bertrand, Chem. Sci. 2013, 4, 3020-3030
3. b) Y. Wang, G. H. Robinson, Dalton Trans. 2012, 41, 337-345
4. c) H. D. Velazquez, F. Verpoort, Chem. Soc. Rev. 2012, 41, 7032-7060
5. d) D. Martin, M. Soleilhavoup, G Bertrand, Chem. Sci. 2011, 2, 389-399
6. e) D. Martin, M. Melaimi, M. Soleilhavoup, G Bertrand, Organometallics 2011, 30, 5304-5313
7. f) M. Melaimi, M. Soleilhavoup, G. Bertrand, Angew. Chem. Int. Ed. 2010, 49, 8810-8849
8. Angew. Chem. 2010, 122, 8992-9032
9. g) W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1290-1309
10. Angew. Chem. 2002, 114, 1342-1363
11. h) D. Bourissou, O. Guerret, F P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-91.
12. V. Lavallo, Y. Canac, C. Präsang, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2005, 44, 5705-5709
13. Angew. Chem. 2005, 117, 5851-5855.
14. G. D. Frey, V. Lavallo, B. Donnadieu, W. W. Schoeller, G Bertrand, Science 2007, 316, 439-441.
15. R. Bertermann, H. Braunschweig, C. K. L. Brown, A. Damme, R. D. Dewhurst, C. Hçrl, T. Kramer, I. Krummenacher, B. Pfaffinger, K. Radacki, Chem. Commun. 2014, 50, 97-99.
16. For background on iminoboranes see: a) P. Paetzold, Adv. Inorg. Chem. 1987, 31, 123-170
17. b) H. Nçth, Angew. Chem. Int. Ed. Engl. 1988, 27, 1603-1623
18. Angew. Chem. 1988, 100, 1664-1684.
19. For more specific examples of iminoborane reactivity see: a) P. Paetzold, Pure Appl. Chem. 1991, 63, 345-350
20. b) P. Paetzold, Phosphorus Sulfur Silicon Relat. Elem. 1994, 93-94, 39-50
21. c) U. Braun, B. Bçck, H. Nçth, I. Schwab, M. Schwartz, S. Weber, U. Wietelmann, Eur. J. Inorg. Chem. 2004, 3612-3628
22. d) D. Männig, H. Nçth, I. Schwab, M. Schwartz, S. Weber, U. Wietelmann, Angew. Chem. Int. Ed. Engl. 1985, 24, 998-999
23. Angew. Chem. 1985, 97, 979-980
24. e) E. Bulak, G E. Herberich, I. Manners, H. Mayer, P. Paetzold, Angew. Chem. Int. Ed. Engl. 1988, 27, 958-959
25. Angew. Chem. 1988, 100, 964-965
26. f) E. Bulak, P. Paetzold, Z. Anorg. Allg. Chem. 2000, 626, 1277-1278
27. g) P. Paetzold, D Hahnfeld, U. Englert, W Wojnowski, B. Dreczewski, Z. Pawelec, L. Walz, Chem. Ber. 1992, 125, 1073-1078
28. h) P. Paetzold, D Hahnfeld, U. Englert, Chem. Ber. 1992, 125, 1079-1081
29. i) P. Paetzold, K. Delpy, R. P. Hughes, W A. Herrmann, Chem. Ber. 1985, 118, 1724-1725
30. j) H. Braunschweig, A. Damme, J. O. C. Jimenez-Halla, B. Pfaffinger, K. Radacki, J. Wolf, Angew. Chem. Int. Ed. 2012, 51, 10034-10037
31. Angew. Chem. 2012, 124, 10177-10180
32. k) H. Braunschweig, K. Geetharani, J. O. C. Jimenez-Halla, M. Schäfer, Angew. Chem. Int. Ed. 2014, 53, 3500-3504
33. Angew. Chem. 2014, 126, 3568-3572.
34. a) J. Bçhnke, H. Braunschweig, W. C. Ewing, C. Hçrl, T. Kramer, I. Krummenacher, J. Mies, A. Vargas, Angew. Chem. Int. Ed. 2014, 53, 9082-9085
35. Angew. Chem. 2014, 126, 9228-9231
36. b) H Braunschweig, R. D Dewhurst, K. Hammond, J. Mies, K. Radacki, A. Vargas, Science 2012, 336, 1420-1422
37. c) P. Bissinger, H. Braunschweig, A. Damme, T. Kupfer, A. Vargas, Angew. Chem. Int. Ed. 2012, 51, 9931-9934
38. Angew. Chem. 2012, 124, 10069-10073
39. d) Y. Wang, B. Quillian, P. Wei, C. S. Wannere, Y Xie, R. B. King, H. F Schaefer III, P. v. R. Schleyer, G H. Robinson, J. Am. Chem. Soc. 2007, 129, 12412-12413.
40. P. Paetzold, C. von Plothoa, G. Schmid, R. Boese, B. Schrader, D Bougeard, U. Pfeiffer, R. Gleiter, W Schäfer, Chem. Ber. 1984, 117, 1089-1102.
41. a) U. Hçbel, H. Nçth, H. Prigge, Chem. Ber. 1986, 119, 325-337
42. b) W. Beck, W. Becker, H. Nçth, B. Wrackmeyer, Chem. Ber. 1972, 105, 2883-2897.
43. a) J. I. Bates, P. Kennepohl, D. P. Gates, Angew. Chem. Int. Ed. 2009, 48, 9844-9847
44. Angew. Chem. 2009, 121, 10028-10031
45. b) J. I. Bates, D. P. Gates, Organometallics 2012, 31, 4529-4536.
46. a) H. Y. Cui, Y. J. Shao, X. F. Li, L. B. Kong, C. M. Cui, Organometallics 2009, 28, 5191-5195
47. b) R. S. Ghadwal, H. W. Roesky, M. Granitzka, D. Stalke, J. Am. Chem. Soc. 2010, 132, 10018-10020.
48. A. J. Arduengo, F. Davidson, H. V R. Dias, J. R. Goerlich, D. Khasnis, W. J. Marshall, T. K. Praasha, J. Am. Chem. Soc. 1997, 119, 12742-12749.
49. J. Münster, P. Paetzold, E. Schrçder, H. Schwan, T von Bennigsen-Mackiewicz, Z. Anorg. Allg. Chem. 2004, 630, 2641-2651.
50. K. C. Mondal, P. P. Samuel, H. W. Roesky, R. R. Aysin, L. A. Leites, S. Neudeck, J. Liibben, B. Dittrich, N Holzmann, M. Hermann, G. Frenking, J. Am. Chem. Soc. 2014, 136, 8919-8922.
51. a) G. B. Butler, G. L. Statton, J. Am. Chem. Soc. 1964, 86, 518
52. b) G. B. Butler, G. L. Statton, W. Brey, Jr., J. Org. Chem. 1965, 30, 4194-4198
53. c) C. L. McCormick, G. B. Butler, J. Org. Chem. 1976, 41, 2803-2808
54. d) R. M. Adams, F.D. Poholsky, Inorg. Chem. 1963, 2, 640-641
55. e) E. P. Mayer, H. Nçth, Chem. Ber. 1993, 126, 1551-1557.
56. During the preparation of this manuscript, Bertrand and Stephan published a molecule with this boraimine structure, though synthesized by a different route: F Dahcheh, D Martin, D W Stephan, G Bertrand, Angew. Chem. Int. Ed. 2014, 53, 13159-13163
57. Angew. Chem. 2014, 126, 13375-13379.
58. For several examples see: a) P. P. Power, Chem. Rev. 1999, 99, 3463-3503
59. b) R. C. Fischer, P. P. Power, Chem. Rev. 2010, 110, 3877-3923.
60. W Baumann, D Michalik, F. Reiß, A. Schulz, A. Villinger, Angew. Chem. Int. Ed. 2014, 53, 3250-3253
61. Angew. Chem. 2014, 126, 3314-3318.
62. CCDC 1024624 (2), 1024641 (3), 1024639 (5), and 1024628 (6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.