Metal-free oxyaminations of alkenes using hydroxamic acids

Journal of the American Chemical Society

Volumn 133, Issue 30, 2011, Pages 11402-11405

  Schmidt, Valerie A ^a   Alexanian, Erik J ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC ALKENES; DIFUNCTIONALIZATION; HYDROXAMIC ACIDS; RADICAL TRAP; REGIOISOMERS;

ORGANIC ACIDS;

OLEFINS;

ALKENE DERIVATIVE; CYCLOALKENE; DICARBOXYLIC ACID DERIVATIVE; DIISOPROPYL AZODICARBOXYLATE; HYDROXAMIC ACID; RADICAL; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; AUTOOXIDATION; CHEMICAL MODIFICATION; CYCLIZATION; OXYAMINATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY;

ALKENES; AMINATION; AZO COMPOUNDS; CYCLIZATION; HYDROXAMIC ACIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79960853853     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja204255e     Document Type: Article

References (27)

1. Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576
2. Donohoe, T. J.; Callens, C. K. A.; Flores, A.; Lacy, A. R.; Rathi, A. H. Chem.-Eur. J. 2011, 17, 58-76
3. Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1 2002, 2733-2746
4. Nilov, D.; Reiser, O. Adv. Synth. Catal. 2002, 344, 1169-1173
5. For examples of transition-metal-catalyzed oxyaminations, see: Os: Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis, 2 nd ed.; Beller, M.; Bolm, C., Eds.; Wiley VCH: Weinheim, 2004; pp 309-326.
6. Donohoe, T. J.; Johnson, P. D.; Helliwell, M.; Keenan, M. Chem. Commun. 2001, 2078-2079
7. Kenworthy, M. N.; Taylor, R. J. K. Org. Biomol. Chem. 2005, 3, 603-611
8. Donohoe, T. J.; Chughtai, M. J.; Klauber, D. J.; Griffin, D.; Campbell, A. D. J. Am. Chem. Soc. 2006, 128, 2514-2515 Pd: Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690-7691
9. Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179-7181 Rh: Beaumont, S.; Pons, V.; Retailleau, P.; Dodd, R. H.; Dauban, P. Angew. Chem., Int. Ed. 2010, 49, 1634-1637 Au: de Haro, T.; Nevado, C. Angew. Chem., Int. Ed. 2011, 50, 906-910 Cu: Michaelis, D. J.; Shaffer, C. J.; Yoon, T. P. J. Am. Chem. Soc. 2007, 129, 1866-1867
10. Fuller, P. H.; Kim, J.-W.; Chemler, S. R. J. Am. Chem. Soc. 2008, 130, 17638-17639
11. Mancheno, D. E.; Thornton, A. R.; Stoll, A. H.; Kong, A.; Blakey, S. B. Org. Lett. 2010, 12, 4110-4113 Fe: Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 4570-4571
12. Liskin, D. V.; Sibbald, P. A.; Rosewall, C. F.; Michael, F. E. J. Org. Chem. 2010, 75, 6294-6296
13. Serna, S.; Tellitu, I.; Dominguez, E.; Moreno, I.; SanMartin, R. Tetrahedron 2004, 60, 6533-6539
14. Wardrop, D. J.; Bowen, E. G.; Forslund, R. E.; Sussman, A. D.; Weerasekera, S. L. J. Am. Chem. Soc. 2010, 132, 1188-1189
15. Lovick, H. M.; Michael, F. E. J. Am. Chem. Soc. 2010, 132, 1249-1251
16. Alewood, P. F.; Hussain, S. A.; Jenkins, T. C.; Perkins, M. J.; Sharma, A. H.; Siew, N. P. Y.; Ward, P. J. Chem. Soc., Perkin Trans. 1 1978, 1066-1076
17. Schmidt, V. A.; Alexanian, E. J. Angew. Chem., Int. Ed. 2010, 49, 4491-4494
18. Shah, A.; George, M. V. Tetrahedron 1971, 27, 1291-1301 For a recent study potentially involving the amination of carbon-centered radicals using azodicarboxylates, see: Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2006, 128, 11693-11712
19. For reactions employing additional azodicarboxylates, see Supporting Information.
20. It is also possible that the azodicarboxylate could contribute to the initiation of the oxyamination process. For an example of an azodicarboxylate facilitating nitroxyl radical formation, see: Grochowski, E.; Boleslawska, T.; Jurczak, J. Synthesis 1977, 718-720
21. Trisubstituted alkenes are not currently viable substrates using the present oxyamination conditions.
22. Alexakis, A.; Lensen, N.; Mangeney, P. Synlett 1991, 625-626
23. For further synthetic transformations of oxyamination products, see Supporting Information.
24. For a direct trans oxyamination of acyclic alkenes, see: Mahoney, J. M.; Smith, C. R.; Johnston, J. N. J. Am. Chem. Soc. 2005, 127, 1354-1355 For a trans oxyamination of cyclic alkenes, see ref 4b.
25. Munz, D.; Strassner, T. J. Org. Chem. 2010, 75, 1491-1497
26. For a survey of radical-mediated domino processes, see: Tietze, L. F.; Brasche, G.; Gericke, K. M. In Domino Reactions in Organic Synthesis; Wiley VCH: Weinheim, 2006; Chapter 3, pp 219-279.
27. For an example of an osmium-catalyzed reaction featuring a tandem tethered oxyamination/oxidative cyclization of dienes, see: Donohoe, T. J.; Lindsay-Scott, P. J.; Parker, J. S. Tetrahedron Lett. 2009, 50, 3523-3526