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C-H Insertion of Rhodium-Carbene Using Diazo Compounds

C-H Insertion of Rhodium-Carbene Using Diazo Compounds

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C-H Insertion of Rhodium-Carbene Using Diazo Compounds

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  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