Catalytic functionalization of unactivated sp3 C-H bonds via exo -directing groups: Synthesis of chemically differentiated 1,2-Diols

Journal of the American Chemical Society

Volumn 134, Issue 41, 2012, Pages 16991-16994

  Ren, Zhi ^a   Mo, Fanyang ^a   Dong, Guangbin ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,2-DIOLS; C-H ACTIVATION; C-H BOND; CATALYTIC FUNCTIONALIZATION; CYCLIC SUBSTRATES; FUNCTIONALIZATIONS; FUNCTIONALIZED; METHINE GROUP; METHYL GROUP; METHYLENE GROUPS; SITE SELECTIVE;

ACTIVATION ANALYSIS; CATALYSIS; FUNCTIONAL GROUPS;

SUBSTRATES;

1,2 DIOL DERIVATIVE; ALCOHOL DERIVATIVE; CARBENE; CARBON; HYDROGEN; MENTHOL; OXIME; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; OXIDATION; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 84867553616     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3082186     Document Type: Article

References (36)

1. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936
2. Chen, K.; Baran, P. S. Nature 2009, 459, 824
3. Simmons, E. M.; Hartwig, J. F. Nature 2012, 483, 70
4. Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857
5. Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362
6. Chen, M. S.; White, M. C. Science 2007, 318, 783
7. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191
9. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
10. Davies, H. M. L. J. Mol. Catal. A: Chem. 2002, 189, 125
11. Wang, X.; Lu, Y.; Dai, H.-D; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203
12. Lu, Y.; Wang, D.-H.; Engle, K. M.; Yu, J-.Q. J. Am. Chem. Soc. 2010, 132, 5916
13. Simmons, E. M.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 17092
14. Gormisky, P. E.; White, M. C. J. Am. Chem. Soc. 2011, 133, 12584
15. Qi, X.; Rice, G. T.; Lall, M. S.; Plummer, M. S.; White, M. C. Tetrahedron 2012, 66, 4816
16. Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156
17. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
18. For a review, see: Hartung, J.; Gottwald, T.; Spehar, K. Synthesis 2002, 11, 1469
19. Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598
20. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935
21. Chen, K.; Richter, J. M.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 7247
22. Michaudel, Q.; Thevenet, D.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 2547
23. Voica, A. F.; Mendoza, A.; Gutekunst, W. R.; Fraga, J. O.; Baran, P. S. Nat. Chem. 2012, 4, 629
24. The directed activation of allylic C-H bonds to form 1,2-diols was first developed by White; see ref 6a.
25. For a synthesis of catechols from phenols via silanol-DGs, see: Huang, C.; Ghavtadze, N.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 17630
26. Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542
27. Neufeldt, S. R.; Sanford, M. S. Org. Lett. 2010, 12, 532
28. For a single example using an oxime as an exo -DG in functionalization aromatic C-H bonds, see: Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285
29. Mawo, R. Y.; Mustakim, S.; Young, V. G., Jr.; Hoffmann, M. R.; Smoliakova, I. P. Organometallics 2007, 26, 1801
30. Keuseman, K. J.; Smoliakova, I. P.; Dunina, V. V. Organometallics 2005, 24, 4159 and references therein
31. 2O in a Pd-catalyzed C-H oxidation reaction, see: Giri, R.; Liang, J.; Lei, J.-G.; Li, J- J.; Wang, D.-H.; Chen, X.; Naggar, I. C.; Guo, C.; Foxman, B. M.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 7420
32. For a related imine-DG in a stoichiometric Pd-mediated C-H activation, see: Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856
33. García Martínez, A.; Teso Vilar, E.; García Fraile, A.; De La Moya Cerero, S.; Martínez Ruiz, P. Tetrahedron: Asymmetry 1998, 9, 1737
34. Olefins react under the reported conditions; see: Li, Y.; Song, D.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2962
35. 3 C-H functionalization, see: Wang, D.-H.; Wu, D.-F.; Yu, J.-Q. Org. Lett. 2006, 8, 3387
36. For a recent Fe-catalyzed C-H activation-initiated skeleton rearrangement, see: Bigi, M. A.; Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2012, 134, 9721