Hydrogenations at room temperature and atmospheric pressure with mesoionic carbene-stabilized borenium catalysts

Angewandte Chemie - International Edition

Volumn 54, Issue 8, 2015, Pages 2467-2471

  Eisenberger, Patrick ^a   Bestvater, Brian P ^a   Keske, Eric C ^a   Crudden, Cathleen M ^a,b  

^a QUEEN S UNIVERSITY   (Canada)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

Borenium; Catalysis; Hydrogenation; Lewis acids; Mesoionic carbenes

Indexed keywords

ATMOSPHERIC PRESSURE; CATALYSIS; CATALYSTS; HYDRIDES; ORGANIC COMPOUNDS;

AMBIENT PRESSURES; BORENIUM; CARBENES; HYDRIDE ABSTRACTION; HYDROGENATION REACTIONS; LEWIS ACID; MESOIONIC CARBENE; ROOM TEMPERATURE;

HYDROGENATION;

BORANE DERIVATIVE; CARBENE; LEWIS ACID; METHANE; TRIAZOLE DERIVATIVE;

ANALOGS AND DERIVATIVES; ATMOSPHERIC PRESSURE; CATALYSIS; CHEMISTRY; CONFORMATION; HYDROGENATION; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

ATMOSPHERIC PRESSURE; BORANES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HYDROGENATION; LEWIS ACIDS; METHANE; MOLECULAR CONFORMATION; TEMPERATURE; TRIAZOLES;

EID: 84922716545     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409250     Document Type: Article

References (48)

1. R. Crabtree, Acc. Chem. Res. 1979, 12, 331-337.
2. J. G. de Vries, C. J. Elsevier, The Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, 2007.
3. a) G. C. Welch, R. R. S. Juan, J. D. Masuda, D. W. Stephan, Science 2006, 314, 1124-1126;
4. b) "Frustrated Lewis Pairs I: Uncovering and Understanding": Topics in Current Chemistry, Vol. 332 (Eds.: G. Erker, D. W. Stephan), Springer, Berlin, 2013.
5. a) P. A. Chase, T. Jurca, D. W. Stephan, Chem. Commun. 2008, 1701-1703;
6. b) P. A. Chase, G. C. Welch, T. Jurca, D. W. Stephan, Angew. Chem. Int. Ed. 2007, 46, 8050-8053;
7. Angew. Chem. 2007, 119, 8196-8199.
8. a) G. Ghattas, D. Chen, F. Pan, J. Klankermayer, Dalton Trans. 2012, 41, 9026-9028;
9. b) D. Chen, Y. Wang, J. Klankermayer, Angew. Chem. Int. Ed. 2010, 49, 9475-9478;
10. Angew. Chem. 2010, 122, 9665-9668;
11. c) D. Chen, J. Klankermayer, Chem. Commun. 2008, 2130-2131;
12. d) Y. Liu, H. Du, J. Am. Chem. Soc. 2013, 135, 6810-6813;
13. e) V. Sumerin, K. Chernichenko, M. Nieger, M. Leskelä, B. Rieger, T. Repo, Adv. Synth. Catal. 2011, 353, 2093-2110;
14. f) Z. M. Heiden, D. W. Stephan, Chem. Commun. 2011, 47, 5729-5731.
15. M. Mewald, R. Fröhlich, M. Oestreich, Chem. Eur. J. 2011, 17, 9406-9414.
16. a) P. Kölle, H. Nöth, Chem. Rev. 1985, 85, 399-418;
17. b) W. E. Piers, S. C. Bourke, K. D. Conroy, Angew. Chem. Int. Ed. 2005, 44, 5016-5036;
18. Angew. Chem. 2005, 117, 5142-5163;
19. c) T. S. De Vries, A. Prokofjevs, E. Vedejs, Chem. Rev. 2012, 112, 4246-4282;
20. d) E. J. Corey, Angew. Chem. Int. Ed. 2009, 48, 2100-2117;
21. Angew. Chem. 2009, 121, 2134-2151.
22. a) V. Bagutski, A. Del Grosso, J. A. Carrillo, I. A. Cade, M. D. Helm, J. R. Lawson, P. J. Singleton, S. A. Solomon, T. Marcelli, M. J. Ingleson, J. Am. Chem. Soc. 2013, 135, 474-487;
23. b) A. Del Grosso, P. J. Singleton, C. A. Muryn, M. J. Ingleson, Angew. Chem. Int. Ed. 2011, 50, 2102-2106;
24. Angew. Chem. 2011, 123, 2150-2154.
25. a) J. R. Lawson, E. R. Clark, I. A. Cade, S. A. Solomon, M. J. Ingleson, Angew. Chem. Int. Ed. 2013, 52, 7518-7522;
26. Angew. Chem. 2013, 125, 7666-7670;
27. b) T. Stahl, K. Müther, Y. Ohki, K. Tatsumi, M. Oestreich, J. Am. Chem. Soc. 2013, 135, 10978-10981.
28. I. A. Cade, M. J. Ingleson, Chem. Eur. J. 2014, 20, 12874.
29. a) D. McArthur, C. P. Butts, D. M. Lindsay, Chem. Commun. 2011, 47, 6650-6652;
30. b) D. M. Lindsay, D. McArthur, Chem. Commun. 2010, 46, 2474-2476.
31. a) A. Prokofjevs, A. Boussonniere, L. F. Li, H. Bonin, E. Lacote, D. P. Curran, E. Vedejs, J. Am. Chem. Soc. 2012, 134, 12281-12288;
32. b) P. Eisenberger, A. M. Bailey, C. M. Crudden, J. Am. Chem. Soc. 2012, 134, 17384-17387;
33. c) S. E. Denmark, Y. Ueki, Organometallics 2013, 32, 6631-6634;
34. d) J. Chen, R. A. Lalancette, F. Jäkle, Chem. Commun. 2013, 49, 4893-4895;
35. e) J. M. Farrell, J. A. Hatnean, D. W. Stephan, J. Am. Chem. Soc. 2012, 134, 15728-15731.
36. a) P. Mathew, A. Neels, M. Albrecht, J. Am. Chem. Soc. 2008, 130, 13534-13535;
37. b) K. F. Donnelly, A. Petronilho, M. Albrecht, Chem. Commun. 2013, 49, 1145-1159.
38. L. B. de Oliveira Freitas, P. Eisenberger, C. M. Crudden, Organometallics 2013, 32, 6635-6638.
39. a) M. Horn, L. H. Schappele, G. Lang-Wittkowski, H. Mayr, A. R. Ofial, Chem. Eur. J. 2013, 19, 249-263;
40. b) M. Horn, H. Mayr, E. Lacote, E. Merling, J. Deaner, S. Wells, T. McFadden, D. P. Curran, Org. Lett. 2012, 14, 82-85.
41. a) E. Aldeco-Perez, A. J. Rosenthal, B. Donnadieu, P. Parameswaran, G. Frenking, G. Bertrand, Science 2009, 326, 556-559;
42. b) S. Gründemann, A. Kovacevic, M. Albrecht, J. W. Faller Robert, H. Crabtree, Chem. Commun. 2001, 2274-2275.
43. See the Supporting Information for details.
44. Y. Liu, H. Du, J. Am. Chem. Soc. 2013, 135, 12968-12971.
45. a) M. A. Beckett, D. S. Brassington, S. J. Coles, M. B. Hursthouse, Inorg. Chem. Commun. 2000, 3, 530-533;
46. b) M. A. Beckett, G. C. Strickland, J. R. Holland, K. Sukumar Varma, Polymer 1996, 37, 4629-4631;
47. c) V. Gutmann, Coord. Chem. Rev. 1976, 18, 225-255;
48. d) G. C. Welch, L. Cabrera, P. A. Chase, E. Hollink, J. D. Masuda, P. Wei, D. W. Stephan, Dalton Trans. 2007, 3407-3414.