Magnesium-Catalyzed Mild Reduction of Tertiary and Secondary Amides to Amines

ACS Catalysis

Volumn 5, Issue 7, 2015, Pages 4219-4226

  Lampland, Nicole L ^a   Hovey, Megan ^a,b   Mukherjee, Debabrata ^a,c   Sadow, Aaron D ^a  

^a IOWA STATE UNIVERSITY   (United States)

^b Oxbow Carbon LLC   (United States)

^c RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

amide reduction; catalysis; deoxygenation; hydroboration; magnesium

Indexed keywords

ADDITION REACTIONS; AMINES; CATALYSIS; CATALYSTS; CHEMICAL ACTIVATION; MAGNESIUM;

AMIDE REDUCTION; C-C BOND CLEAVAGES; CATALYST ACTIVATION; CATALYTIC ACTIVATION; CATALYTIC INTERMEDIATES; DEOXYGENATIONS; HYDROBORATION; MILD REACTION CONDITIONS; KINETIC EXPERIMENT;

AMIDES;

EID: 84946151127     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b01038     Document Type: Article

References (39)

1. Lawrence, S. A. Amines: synthesis, properties, and applications; Cambridge University Press: New York, 2004.
2. Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L., Jr.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411-420 10.1039/b703488c
3. Smith, A. M.; Whyman, R. Chem. Rev. 2014, 114, 5477-5510 10.1021/cr400609m
4. 6. In Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Industries; Dunn, P. J.; Hii, K. K.; Krische, M. J.; Williams, M. T., Eds.; Wiley: Hoboken, NJ, 2013; pp 1-36.
5. Gaylord, N. G. Reduction with Complex Metal Hydrides; Interscience: New York, 1956.
6. Brown, H. C. Hydroboration. W. A. Benjamin: New York, 1962.
7. Igarashi, M.; Fuchikami, T. Tetrahedron Lett. 2001, 42, 1945-1947 10.1016/S0040-4039(01)00039-9
8. Cheng, C.; Brookhart, M. J. Am. Chem. Soc. 2012, 134, 11304-11307 10.1021/ja304547s
9. Park, S.; Brookhart, M. J. Am. Chem. Soc. 2012, 134, 640-653 10.1021/ja209567m
10. Das, S.; Addis, D.; Junge, K.; Beller, M. Chem.-Eur. J. 2011, 17, 12186-12192 10.1002/chem.201101143
11. Li, Y.; Molina de La Torre, J. A.; Grabow, K.; Bentrup, U.; Junge, K.; Zhou, S.; Brückner, A.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 11577-11580 10.1002/anie.201304495
12. Reeves, J. T.; Tan, Z.; Marsini, M. A.; Han, Z. S.; Xu, Y.; Reeves, D. C.; Lee, H.; Lu, B. Z.; Senanayake, C. H. Adv. Synth. Catal. 2013, 355, 47-52 10.1002/adsc.201200835
13. Stein, M.; Breit, B. Angew. Chem., Int. Ed. 2013, 52, 2231-2234 10.1002/anie.201207803
14. Li, B.; Sortais, J.-B.; Darcel, C. Chem. Commun. 2013, 49, 3691-3693 10.1039/c3cc39149c
15. Hanada, S.; Ishida, T.; Motoyama, Y.; Nagashima, H. J. Org. Chem. 2007, 72, 7551-7559 10.1021/jo070591c
16. Zhou, S.; Junge, K.; Addis, D.; Das, S.; Beller, M. Org. Lett. 2009, 11, 2461-2464 10.1021/ol900716q
17. Balaraman, E.; Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 16756-16758 10.1021/ja1080019
18. Barrios-Francisco, R.; Balaraman, E.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2013, 32, 2973-2982 10.1021/om400194w
19. Hanada, S.; Tsutsumi, E.; Motoyama, Y.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 15032-15040 10.1021/ja9055307
20. Fernandes, A. C.; Romão, C. C. J. Mol. Catal. A: Chem. 2007, 272, 60-63 10.1016/j.molcata.2007.03.019
21. Xie, W.; Zhao, M.; Cui, C. Organometallics 2013, 32, 7440-7444 10.1021/om400951n
22. Das, S.; Addis, D.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2010, 132, 1770-1771 10.1021/ja910083q
23. Sakai, N.; Fujii, K.; Konakahara, T. Tetrahedron Lett. 2008, 49, 6873-6875 10.1016/j.tetlet.2008.09.086
24. Chong, C. C.; Kinjo, R. ACS Catal. 2015, 5, 3238-3259 10.1021/acscatal.5b00428
25. Arrowsmith, M.; Hadlington, T. J.; Hill, M. S.; Kociok-Köhn, G. Chem. Commun. 2012, 48, 4567-4569 10.1039/c2cc30565h
26. Arrowsmith, M.; Hill, M. S.; Hadlington, T.; Kociok-Köhn, G.; Weetman, C. Organometallics 2011, 30, 5556-5559 10.1021/om2008138
27. Anker, M. D.; Arrowsmith, M.; Bellham, P.; Hill, M. S.; Kociok-Köhn, G.; Liptrot, D. J.; Mahon, M. F.; Weetman, C. Chem. Sci. 2014, 5, 2826-2830 10.1039/c4sc00885e
28. Arrowsmith, M.; Hill, M. S.; Kociok-Köhn, G. Chem.-Eur. J. 2013, 19, 2776-2783 10.1002/chem.201203190
29. Mukherjee, D.; Ellern, A.; Sadow, A. D. Chem. Sci. 2014, 5, 959-964 10.1039/C3SC52793J
30. Guthrie, J. P. J. Am. Chem. Soc. 1974, 96, 3608-3615 10.1021/ja00818a039
31. Brown, H. C.; Heim, P. J. Am. Chem. Soc. 1964, 86, 3566-3567 10.1021/ja01071a037
32. Brown, H. C.; Heim, P. J. Org. Chem. 1973, 38, 912-916 10.1021/jo00945a015
33. Bontemps, S.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2013, 52, 10253-10255 10.1002/anie.201304025
34. Oshima, K.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 7324-7327 10.1021/ja2020229
35. Koren-Selfridge, L.; Londino, H. N.; Vellucci, J. K.; Simmons, B. J.; Casey, C. P.; Clark, T. B. Organometallics 2009, 28, 2085-2090 10.1021/om801228m
36. Ohmura, T.; Masuda, K.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 1526-1527 10.1021/ja073896h
37. Naulet, N.; Filleux, M. L.; Martin, G. J.; Pornet, J. Org. Magn. Reson. 1975, 7, 326-30 10.1002/mrc.1270070707
38. Pawlikowski, A. V.; Gray, T. S.; Schoendorff, G.; Baird, B.; Ellern, A.; Windus, T. L.; Sadow, A. D. Inorg. Chim. Acta 2009, 362, 4517-4525 10.1016/j.ica.2009.06.017
39. Kidd, R. G. Boron-11. Academic Press: New York, 1983; Vol. 2, p 49-77.