1 / 40

C-H Insertion of Rhodium-Carbene Using Diazo Compounds

C-H Insertion of Rhodium-Carbene Using Diazo Compounds. Presented by Pascal Cérat Litterature Meeting 6 april 2010. Carbenes. Metal Carbenes in Organic Synthesis ; Dörwald, F. G., Ed.; Wiley-VCH: Weinheim, 1999.

jenski
Download Presentation

C-H Insertion of Rhodium-Carbene Using Diazo Compounds

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. C-H Insertion of Rhodium-Carbene Using Diazo Compounds Presented by Pascal Cérat Litterature Meeting 6 april 2010

  2. Carbenes Metal Carbenes in Organic Synthesis; Dörwald, F. G., Ed.; Wiley-VCH: Weinheim, 1999. Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev.2000, 100, 39.

  3. Metal-Carbenes 3 Metal Carbenes in Organic Synthesis; Dörwald, F. G., Ed.; Wiley-VCH: Weinheim, 1999.

  4. Synthesis of Diazo Compounds 4 Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-VCH: New York, 1998.

  5. Reactivity of Diazo Compounds 5 Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-VCH: New York, 1998. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  6. C-H Insertion by Carbenes Doering, W. v. E.; Buttery, R. G.; Laughlin, R. G.; Chaudhuri, N. J. Am. Chem. Soc.1956, 78, 3224. Doering, W. v. E.; Knox, L. H. J. Am. Chem. Soc.1956, 78, 4947. Greuter, F.; Kalvoda, J.; Jeger, O. Proc. Chem. Soc. 1958, 348. Yates, P.; Danishefsky, S. J. Am. Chem. Soc.1962, 84, 879. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704. 6

  7. Introduction of Rhodium C-H Insertion Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssié, P. J. Chem. Soc. Chem. Commun.1981, 688. Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssié, P. Bull. Soc. Chim. Belg.1984, 93, 945. Wenkert, E.; Davis, L. L.; Mylari, B. L.; Solomon, M. F.; Da Silva, R. R.; Shulman, S.; Warnet, R. J. J. Org. Chem.1982, 47, 3242. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704. 7

  8. Propreties of Rhodium 8 Padwa, A.; Austin, D. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1797. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  9. C-H Insertion vs C-H Activation 9 Davies, H. M.; Manning, J. R. Nature2008, 451, 417. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  10. General Mechanism of C-H Insertion 10 Nakamura, E.; Yoshikai, N.; Yamanaka, M. J. Am. Chem. Soc.2002, 124, 7181.

  11. General Mechanism of C-H Insertion 11 Nakamura, E.; Yoshikai, N.; Yamanaka, M. J. Am. Chem. Soc.2002, 124, 7181.

  12. Intramolecular C-H insertion: Regioselectivity 12 Taber, D. F.; Petty, E. H. J. Org. Chem.1982, 47, 4808. Taber, D. H.; Ruckle, R. E., Jr. J. Am. Chem. Soc.1986, 108, 7686.

  13. Regioselectivity Modulated by Electronic Effect of the C-H 13 Stork, G.; Nakatani, K. Tet. Lett.1988, 29, 2283. Spero, D. M.; Adams, J. Tet. Lett.1992, 33, 1143. Davies, H. M.; Manning, J. R. Nature2008, 451, 417.

  14. Changing the a-Group of the Diazo 14 Yoon, C. H.; Zaworotko, M. J.; Moulton, B.; Jung, K. W. Org. Lett.2001, 3, 3539. Gois, P. M. P.; Afonso, A. M. Eur. J. Org. Chem.2003, 3798.

  15. Impact of the Ligands on Regioselectivity Doyle, M. P.; Tauton, J.; Pho, H. Q. Tet. Lett. 1989, 30, 5397. Doyle, M. P.; Bagheri, V.; Pearson, M. M.; Edwards, J. D. Tet. Lett. 1989, 30, 7001. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc.1993, 115, 958. Padwa, A.; Austin, D. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1797. 15

  16. Impact of the Ligands on Chemioselectivity Padwa, A.; Austin, D. J.; Price, A. T.; Semones, M. A.; Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Tran, A. J. Am. Chem. Soc.1993, 115, 8669. Estevan, F.; Lahuerta, P.; Pérez-Prieto, J.; Sanau, M.; Stiriba, S.-E.; Ubeda, M. A. Organometallics1997, 16, 880. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704. 16

  17. Influence of Ligand on Dirhodium(II) Carbene 17 Lloret, J.; Carbo, J. J.; Bo, C.; Lledos, A.; Pérez-Prieto, J. Organometallics2008, 27, 2873.

  18. Diastereoselectivity in C-H insertion 18 Taber, D. F.; You, K. K.; Rheingold, A. J. Am. Chem. Soc.1996, 118, 547.

  19. Chiral Dirhodium Catalyst in C-H Insertion 19 Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  20. Carboxylates in Intramolecular C-H Insertion 20 Anada, M.; Kitagaki, S.; Hashimoto, S. Heterocycles2000, 52, 875.

  21. Carboxylates in Intramolecular C-H Insertion 21 Anada, M.; Kitagaki, S.; Hashimoto, S. Heterocycles2000, 52, 875.

  22. Carboxylates in Intramolecular C-H Insertion 22 Davies, H. M.; Grazini, M. V. A.; Aouad, E. Org. Lett.2001, 3, 1475. Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. 2002, 4, 3887. Reddy, R. P.; Lee, G. H.; Davies, H. M. L. Org. Lett.2006, 8, 3437.

  23. Carboxamidates in Intramolecular C-H Insertion Doyle, M. P.; Oeveren, A. v.; Westrum, L. J.; Protopopova, M. N.; Clayton, T. W., Jr. J. Am. Chem. Soc.1991, 113, 8982. Doyle, M. P.; Dyatkhin, A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; Basten, A. v. J. Am. Chem. Soc.1994, 116, 4507. Doyle, M. P.; Forbes, D. C. Chem. Rev.1998, 98, 911. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704. 23

  24. Understanding the Utility of Carboxamidate as Ligands 24 Doyle, M. P.; Oeveren, A. v.; Westrum, L. J.; Protopopova, M. N.; Clayton, T. W., Jr. J. Am. Chem. Soc.1991, 113, 8982. Yoshikai, N.; Nakamura, E. Adv. Synth. Catal. 2003, 345, 1159. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  25. Understanding the Utility of Carboxamidate as Ligands 25 Doyle, M. P.; Oeveren, A. v.; Westrum, L. J.; Protopopova, M. N.; Clayton, T. W., Jr. J. Am. Chem. Soc.1991, 113, 8982. Yoshikai, N.; Nakamura, E. Adv. Synth. Catal. 2003, 345, 1159. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  26. Understanding the Utility of Carboxamidate as Ligands 26 Doyle, M. P.; Morgan, J. P.; Fettinger, J. C.; Zavalij, P. Y.; Colyer, J. T.; Timmons, D. J.; Carbucci, M. D. J. Org. Chem.2005, 70, 5291. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  27. Diastereoselectivity with Dirhodium Carboxamidates 27 Doyle, M. P.; Morgan, J. P.; Fettinger, J. C.; Zavalij, P. Y.; Colyer, J. T.; Timmons, D. J.; Carbucci, M. D. J. Org. Chem.2005, 70, 5291. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  28. Use of Othometalated Aryl Phosphine Ligands 28 Estevan, F.; Herbst, K.; Lahuerta, P.; Barberis, M.; Perez-Prieto, J. Organometallics2001, 20, 950. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  29. Intermolecular C-H Insertion Reactions 29 Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  30. Aryldiazoacetate in Intermolecular C-H Insertion Reactions 30 Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  31. Aryldiazoacetate in Intermolecular C-H Insertion Reactions Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509. Davies, H. M. L.; Venkatarmani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. Davies, H. M. L.; Beckwith, R. E. J.; Antoulinakis, E. G.; Jin, Q. J. Org. Chem.2003, 68, 6126. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704. 31

  32. Aryldiazoacetate in Intermolecular C-H Insertion Reactions 32 Davies, H. M. L.; Venkatarmani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. Davies, H. M. L.; Beckwith, R. E. J.; Antoulinakis, E. G.; Jin, Q. J. Org. Chem.2003, 68, 6126.

  33. Aryldiazoacetate in Intermolecular C-H Insertion Reactions 33 Davies, H. M. L.; Hedley, S. J.; Bohall, B.R. J. Org. Chem.2005, 70, 10737.

  34. Vinyldiazoacetate in Intermolecular C-H Insertion Reactions 34 Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett.1999, 1, 233. Davies, H. M. L.; Manning, J. R. Nature2008, 451, 417.

  35. Intermolecular C-H Insertion – Cope Rearrangement Davies, H. M. L.; Jin, Q. J. Am. Chem. Soc.2004, 126, 10862. Davies, H. M. L.; Nikolai, J. Org. Biomol. Chem.2005, 3, 4176. Davies, H. M. L.; Manning, J. R. Nature2008, 451, 417. 35

  36. Intermolecular C-H Insertion – Cope Rearrangement 36 Davies, H. M. L.; Jin, Q. J. Am. Chem. Soc.2004, 126, 10862. Davies, H. M. L.; Nikolai, J. Org. Biomol. Chem.2005, 3, 4176.

  37. Intermolecular C-H Insertion – Cope Rearrangement Davies, H. M. L.; Walji, A. M. Angew. Chem. Int. Ed.2005, 44, 1733. Davies, H. M. L.; Nikolai, J. Org. Biomol. Chem.2005, 3, 4176. Davies, H. M. L.; Dai, X.; Long, M. S. J. Am. Chem. Soc.1996, 128, 2485. Davies, H. M. L.; Manning, J. R. Nature2008, 451, 417. 37

  38. Intermolecular C-H Insertion – Cope Rearrangement Davies, H. M. L.; Walji, A. M. Angew. Chem. Int. Ed.2005, 44, 1733. Davies, H. M. L.; Nikolai, J. Org. Biomol. Chem.2005, 3, 4176. Davies, H. M. L.; Dai, X.; Long, M. S. J. Am. Chem. Soc.1996, 128, 2485. Davies, H. M. L.; Manning, J. R. Nature2008, 451, 417. 38

  39. Conclusion 39 Davies, H. M. L.; Manning, J. R. Nature2008, 451, 417. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.

  40. Conclusion 40

More Related