Dehydrogenative Oxidation of Primary Amines to Nitriles

Synlett

Volumn 25, Issue 17, 2014, Pages 2385-2389

  Tseng, Kuei Nin T ^a   Szymczak, Nathaniel K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

amines; chemoselectivity; dehydrogenation; homogeneous catalysis; nitriles

Indexed keywords

AMINE; NITRILE;

AMINE OXIDATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DEHYDROGENATION; DEHYDROGENATIVE OXIDATION; MATHEMATICAL ANALYSIS; OXIDATION; OXIDATIVE COUPLING; SPECTROSCOPY;

EID: 85027947780     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0034-1378543     Document Type: Article

References (49)

1. Fleming F. F. Nat. Prod. Rep.: 1999; 16 597
2. Fleming F. F., Yao L., Ravikumar P. C., Funk L., Shook B. C. J. Med. Chem.: 2010; 53 7902
3. Pollak P., Romeder G., Hagedorn F., Gelbke H.-P. In Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Weinheim: 2012
4. Sheldon R. A., Kochi J. K. Metal-Catalyzed Oxidations of Organic Compounds. Academic Press New York: 1981
5. Nicolaou K. C., Mathison C. J. N. Angew. Chem. Int. Ed.: 2005; 44 5992
6. Schumperli M. T., Hammond C., Hermans I. ACS Catal.: 2012; 2 1108
7. Dobereiner G. E., Crabtree R. H. Chem. Rev.: 2010; 110 681
8. Murahashi S.-I, Imada Y. In Transition Metals for Organic Synthesis. Wiley-VCH Weinheim: 2008; 497
9. Yamaguchi K., Mizuno N. Angew. Chem. Int. Ed.: 2003; 42 1480
10. Kim J., Stahl S. S. ACS Catal.: 2013; 3 1652
11. Cristian L., Nica S., Pavel O. D., Mihailciuc C., Almasan V., Coman S. M., Hardacre C., Parvulescu V. I. Catal. Sci. Tech.: 2013; 3 2646
12. Yoshida T., Okano T., Otsuka S. J. Chem. Soc., Chem. Commun.: 1979; 870
13. Bernskoetter W. H., Brookhart M. Organometallics: 2008; 27 2036
14. Wang Z., Belli J., Jensen C. M. Faraday Discuss.: 2011; 151 297
15. Tseng K.-N T., Rizzi A. M., Szymczak N. K. J. Am. Chem. Soc.: 2013; 135 16352
16. Okano K., Saito Y., Ogino Y. Bull. Chem. Soc. Jpn.: 1972; 45 69
17. Friedrich A., Schneider S. ChemCatChem: 2009; 1 72
18. Gunanathan C., Milstein D. Science: 2013; 341
19. Hamid M. H. S. A, Slatford P. A., Williams J. M. J. Adv. Synth. Catal.: 2007; 349 1555
20. Zhang J., Leitus G., Ben-David Y., Milstein D. J. Am. Chem. Soc.: 2005; 127 10840
21. Gunanathan C., Ben-David Y., Milstein D. Science: 2007; 317 790
22. Nielsen M., Alberico E., Baumann W., Drexler H.-J, Junge H., Gladiali S., Beller M. Nature (London, U.K.): 2013; 495 85
23. Rodríguez-Lugo R. E., Trincado M., Vogt M., Tewes F., Santiso-Quinones G., Grützmacher H. Nat. Chem.: 2013; 5 342
24. Spasyuk D., Smith S., Gusev D. G. Angew. Chem. Int. Ed.: 2012; 51 2772
25. Tseng K.-N T., Kampf J. W., Szymczak N. K. Organometallics: 2013; 32 2046
26. Fujita K.-i, Tanaka Y., Kobayashi M., Yamaguchi R. J. Am. Chem. Soc.: 2014; 136 4829
27. Wu J., Talwar D., Johnston S., Yan M., Xiao J. Angew. Chem. Int. Ed.: 2013; 52 6983
28. Prades A., Peris E., Albrecht M. Organometallics: 2011; 30 1162
29. Yi C. S., Lee D. W. Organometallics: 2009; 28 947
30. Yoshimura N., Moritani I., Shimamura T., Murahashi S. J. Am. Chem. Soc.: 1973; 95 3038
31. Shvo Y., Laine R. M. J. Chem. Soc., Chem. Commun.: 1980; 753
32. Bui The K., Concilio C., Porzi G. J. Organomet. Chem.: 1981; 208 249
33. Conley B. L., Pennington-Boggio M. K., Boz E., Williams T. J. Chem. Rev.: 2010; 110 2294
34. Anguille S., Brunet J.-J, Chu N. C., Diallo O., Pages C., Vincendeau S. Organometallics: 2006; 25 2943
35. Crabtree R. H. Energy Environ. Sci.: 2008; 1 134
36. http://www.nist.gov.
37. Oae S. Organic Sulfur Chemistry: Structure and Mechanism. CRC Press Boca Raton, FL: 1991
38. Sandmeyer T. Ber. Dtsch. Chem. Ges.: 1885; 18 1492
39. Sandmeyer T. Ber. Dtsch. Chem. Ges.: 1885; 18 1496
40. Rosenmund K. W., Struck E. Ber. Dtsch. Chem. Ges.: 1919; 52 1749
41. Clapham S. E., Hadzovic A., Morris R. H. Coord. Chem. Rev.: 2004; 248 2201
42. Tseng, K. T.; Hale, L. V. A.; Kampf, J. W.; Szymczak, N. K. manuscript in preparation.
43. http://www1.eere.energy.gov/vehiclesandfuels/pdfs/ program/hstt-roadmap-june2013.pdf.
44. Grellier M., Sabo-Etienne S. Dalton Trans.: 2014; 43 6283
45. Pez G. P., Scott A. R., Cooper A. C., Cheng H. US 7101530: 2006
46. Pez G. P., Scott A. R., Cooper A. C., Cheng H., Wilhelm F. C., Abdourazak A. H. US 7351395: 2008
47. http://www.hydrogen.energy.gov/pdfs/review13/ st098-jensen-2013-o.pdf.
48. Reguillo R., Grellier M., Vautravers N., Vendier L., Sabo-Etienne S. J. Am. Chem. Soc.: 2010; 132 7854
49. Compound 2: catalogue no. 794406; compound 3: catalogue no. 794414 (Sigma-Aldrich).