Pd-catalyzed transfer hydrogenolysis of primary, secondary, and tertiary benzylic alcohols by formic acid: A mechanistic study

ACS Catalysis

Volumn 3, Issue 4, 2013, Pages 635-642

  Sawadjoon, Supaporn ^a   Lundstedt, Anna ^a   Samec, Joseph S M ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

alcohols; heterogeneous catalysis; kinetic isotope effect; transfer hydrogenolysis

Indexed keywords

CATALYTIC AMOUNTS; COMPETITIVE INHIBITION; DISPROPORTIONATION REACTIONS; FIRST-ORDER DEPENDENCE; HYDRIDE TRANSFERS; KINETIC ISOTOPE EFFECTS; MECHANISTIC STUDIES; PALLADIUM-CATALYZED;

ALCOHOLS; CARRIER MOBILITY; CATALYSIS; DEUTERIUM; ETHANOL; FORMIC ACID; HYDROGENOLYSIS; KETONES;

HYDROLYSIS;

EID: 84875958807     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs300785r     Document Type: Article

References (40)

1. Yasuda, M.; Onishi, Y.; Ueba, M.; Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741-7744
2. Radinov, R.; Hutchings, S. D. Tetrahedron Lett. 1999, 40, 8955-8960
3. Muzart, J. Tetrahedron 2005, 61, 9423-9463
4. Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044-4098
5. Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411-2502
6. Zakzeski, J.; Bruijnincx, P. C. A.; Jogerius, A. L.; Weckhuysen, B. M. Chem. Rev. 2010, 110, 3552-3599
7. Vedejs, E. Org. React. 1975, 22, 401-422
8. Todd, D. Org. React. 1948, 4, 378-422
9. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585
10. Schlaf, M. J. Chem. Soc., Dalton Trans. 2006, 4645-4653
11. Alonso, D. M.; Bond, J. Q.; Dumesic, J. Green Chem. 2010, 12, 1493-1513
12. Feng, J.; Yang, C.; Zhang, D.; Wang, J.; Fu, H.; Chen, H.; Li, X. Appl. Catal., A 2009, 354, 38-43
13. Liu, X.; Lu, G.; Guo, Y.; Guo, Y.; Wang, Y.; Wang, X. J. Mol. Catal A: Chem. 2006, 252, 176-180
14. Thakar, N.; Polder, N. F.; Djanashvili, K.; van Bekkum, H.; Kapteijn, F.; Moulijn, J. A. J. Catal. 2007, 246, 344-350
15. Kieboom, A. P. G.; de Kreuk, J. F.; van Bekkum, H. J. Catal. 1971, 20, 58-66
16. Taher, D.; Thibault, M. E.; Di Mondo, D.; Jennings, M.; Schlaf, M. Chem.-Eur. J. 2009, 15, 10132-10143
17. Ranade, V. S.; Prins, R. Chem.-Eur. J. 2000, 6, 313-320
18. Jessop, P. G.; Joo, F.; Tai, C.-C. Coord. Chem. Rev. 2004, 248, 2425-2442
19. Federsel, C.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 6254-6257
20. Sheldon, R. A. Pure Appl. Chem. 2000, 72, 1233-1246
21. Trost, B. M. Science 1991, 254, 1471-1477
22. Rylander, P. N. Catalytic Hydrogenation over Platinum Metals; Academic Press: New York, 1967.
23. Kwak, B.-S.; Kim, T.-J.; Lee, S.-I. Appl. Catal., A 2003, 238, 141-148
24. Arceo, E.; Marsden, P.; Bergman, R. G.; Ellman, J. A. Chem. Commun. 2009, 3357-3359
25. Rajagopal, S.; Spatola, A. F. Appl. Catal., A 1997, 152, 69-81
26. Watkins, S. T.; Bowden, S. T. J. Chem. Soc. 1940, 1333-1334
27. Miller, K. J.; Abu-Omar, M. M. Eur. J. Org. Chem. 2003, 1294-1299
28. Saulnier, D. G.; Dodier, M.; Frennesson, D. B.; Langley, D. R.; Vyas, D. M. Org. Lett. 2009, 11, 5154-5157
29. Wiener, H.; Blum, J.; Sasson, Y. J. Org. Chem. 1991, 56, 6145-6148
30. Ahlquist, M.; Fabrizi, G.; Cacchi, S.; Norrby, P.-O. J. Am. Chem. Soc. 2006, 128, 12785-12793
31. Mirzaei, A.; Biswas, S.; Samec, J. S. M. Synthesis 2012, 44, 1213-1218
32. Sawadjoon, S.; Samec, J. S. M. Org. Biomol. Chem. 2011, 9, 2548-2554
33. Howard, F.; Sawadjoon, S.; Samec, J. S. M. Tetrahedron Lett. 2010, 51, 4208-4011
34. Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2003, 198, 317-341
35. Lange, S.; Leitner, W. J. Chem. Soc., Dalton Trans. 2002, 752-758
36. Leitner, W.; Brown, J. M.; Brunner, H. J. Am. Chem. Soc. 1993, 115, 152-159
37. Darenbourg, D. J.; Wiegreffe, P.; Riordan, C. G. J. Am. Chem. Soc. 1990, 112, 5759-5762
38. Yu, J.; Spencer, J. B. Chem. Commun 1998, 1935-1936
39. Casey, C. P.; Singer, S. W.; Powell, D. R.; Hayashi, R. K.; Kavana, M. J. Am. Chem. Soc. 2001, 123, 1090-1100
40. Muzart, J. Tetrahedron 2003, 59, 5789-5816