Selective oxidation of aliphatic C-H bonds in the synthesis of complex molecules

Angewandte Chemie - International Edition

Volumn 47, Issue 15, 2008, Pages 2740-2742

  Christmann, Mathias ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

C H activation; Iron; Natural products; Oxidation

Indexed keywords

CHEMICAL MODIFICATION; CHEMICAL OXYGEN DEMAND; CHEMICAL REACTIONS; IRON COMPOUNDS; OXIDATION; RAW MATERIALS; SYNTHESIS (CHEMICAL);

ARTEMISININ; C-H ACTIVATION; C-H BONDS; CHEMICAL EQUATIONS; COMPLEX MOLECULES; IRON; METAL CATALYSTS; MODEL REACTIONS; NATURAL PRODUCTS; OXIDATION REACTIONS; SELECTIVE OXIDATION; SYNTHESIS OF; TOTAL SYNTHESIS;

COMPLEXATION;

EID: 44349148129     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705766     Document Type: Short Survey

References (32)

1. Handbook of C-H Transformations (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005.
2. A. R. Dick, M. S. Sanford, Tetrahedron 2006, 62, 2439.
3. S. Tanase, E. Bouwman, Adv. Inorg. Chem. 2006, 58, 29.
4. H.-J. Schneider, W. Müller, J. Org. Chem. 1985, 50, 4609.
5. R. Mello, M. Fiorentino, C. Fusco, R. Curci, J. Am. Chem. Soc. 1989, 111, 6749.
6. D. D. DesMarteau, A. Donadelli, V. Montanari, V. A. Petrov, G. Resnati, J. Am. Chem. Soc. 1993, 115, 4897.
7. B. Meunier, Chem. Rev. 1992, 92, 1411.
8. a) B. J. Wallar, J. D. Lipscomb, Chem. Rev. 1996, 96, 2625;
9. b) M. Merkx, D. A. Kopp, M. H. Sazinsky, J. L. Blazyk, J. Müller, S. J. Lippard, Angew. Chem. 2001, 113, 2860;
10. Angew. Chem. Int. Ed. 2001, 40, 2782.
11. R. E. Norman, S. Yan, L. Que, Jr., G. Backes, J. Ling, J. Sanders-Loehr, J. H. Zhang, C. J. O'Connor, J. Am. Chem. Soc. 1990, 112, 1554.
12. C. Kim, K. Chen, J. Kim, L. Que, Jr., J. Am. Chem. Soc. 1997, 119, 5964.
13. T. Okuno, S. Ito, S. Ohba, Y. Nishida, J. Chem. Soc. Dalton Trans. 1997, 3547.
14. K. Chen, L. Que, Jr., Chem. Commun. 1999, 1375.
15. Optically pure 2,2′-bipyrrolidine can be obtained by photodimerization of pyrrolidine (Crabtree) followed by resolution with tartaric acid: a) R. R. Ferguson, C. G. Boojamra, S. H. Brown, R. H. Crabtree, Heterocycles 1989, 28, 121;
16. b) T. Oishi, M. Hirama, L. R. Sita, S. Masamune, Synthesis 1991, 789;
17. c) S. E. Denmark, J. Fu, M. J. Lawler, Org. Synth. 2006, 83, 121.
18. a) M. Hirama, T. Oishi, S. Ito, J. Chem. Soc. Chem. Commun. 1989, 665.
19. M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194.
20. For pertinent discussion concerning the effect of acetic acid, see: R. Mas-Ballesté, L. Que, Jr., J. Am. Chem. Soc. 2007, 129, 15964.
21. M. S. Chen, M. C. White, Science 2007, 318, 783.
22. B. M. Trost, J. L. Gunzner, O. Dirat, Y. H. Rhee, J. Am. Chem. Soc. 2002, 124, 10396.
23. A. Hinman, J. Du Bois, J. Am. Chem. Soc. 2003, 125, 11510.
24. C. G. Espino, J. Du Bois, Angew. Chem. 2001, 113, 618;
25. Angew. Chem. Int. Ed. 2001, 40, 598.
26. P. M. Wehn, J. Du Bois, J. Am. Chem. Soc. 2002, 124, 12950.
27. M.-K. Wong, N.-W. Chung, L. He, X.-C. Wang, Z. Yan, Y.-C. Tang, D. Yang, J. Org. Chem. 2003, 68, 6321.
28. For carboxylic acid directing groups, the addition of acetic acid was omitted.
29. In less obvious situations, DFT calculations or X-ray structures were used to estimate site-specificity.
30. J. Zhan, H. Guo, J. Dai, Y. Zhang, D. Guo, Tetrahedron Lett. 2002, 43, 4519.
31. For an insightful discussion, see: P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404.
32. A. M. Walji, D. W. C. MacMillan, Synlett 2007, 1477.