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Sébastien R. Goudreau

Diaryliodonium Salts in Coupling Reactions. Sébastien R. Goudreau. Literature Meeting. November 9 th , 2009. Cross-Coupling: General Mechanism. Oxidative Addition Favored by Electron-Rich Palladium and Electron-Poor R group. Substitution (trans-metalation)

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Sébastien R. Goudreau

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  1. Diaryliodonium Salts in Coupling Reactions Sébastien R. Goudreau Literature Meeting November 9th, 2009

  2. Cross-Coupling: General Mechanism Oxidative Addition Favored by Electron-Rich Palladium and Electron-Poor R group Substitution (trans-metalation) Favored by Electron-Poor Palladium and Electron-Rich Nu group N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.

  3. Cross-Coupling: General Mechanism X = I > OTf > Br >>> Cl diaryliodonium salts 106 faster then X = I N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.

  4. Reactivity P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178. E. A. Merritt, B. Olofsson, Angew. Chem., Int. Ed. 2009, ASAP

  5. Reactivity P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178. E. A. Merritt, B. Olofsson, Angew. Chem., Int. Ed. 2009, ASAP

  6. Nucleophiles P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178. E. A. Merritt, B. Olofsson, Angew. Chem., Int. Ed. 2009, ASAP

  7. Cross-Coupling

  8. Suzuki Cross-Coupling Reaction N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.

  9. Suzuki Cross-Coupling Reaction N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.

  10. Suzuki Cross-Coupling Reaction High yield without Base ! S.-K. Kang, H.-W. Lee, S.-B. Jang, P.-S. Ho, J. Org. Chem. 1996, 61, 4720-4724.

  11. Suzuki Cross-Coupling Reaction S.-K. Kang, H.-W. Lee, S.-B. Jang, P.-S. Ho, J. Org. Chem. 1996, 61, 4720-4724.

  12. Suzuki Cross-Coupling Reaction S.-K. Kang, H.-W. Lee, S.-B. Jang, P.-S. Ho, J. Org. Chem. 1996, 61, 4720-4724.

  13. Suzuki Cross-Coupling Reaction S.-K. Kang, H.-W. Lee, S.-B. Jang, P.-S. Ho, J. Org. Chem. 1996, 61, 4720-4724.

  14. Copper-Catalyzed “Suzuki-Type” Reaction Boronic acids Reaction did not work with ArI S.-K. Kang, T. Yamaguchi, T.-H. Kim, P.-S. Ho, J. Org. Chem. 1996, 61, 9082-9083.

  15. Copper-Catalyzed “Suzuki-Type” Reaction S.-K. Kang, T. Yamaguchi, T.-H. Kim, P.-S. Ho, J. Org. Chem. 1996, 61, 9082-9083.

  16. Carbonylative Copper-Catalyzed “Suzuki-Type” Reaction Diaryliodonium salts work in all cross coupling reactions ! J.-M. Becht, C. L. Drian, Org. Lett. 2008, 10, 3161-3164. S.-K. Kang, H.-C. Ryu, J.-W. Kim, Synth. Commun. 2001, 31, 1021 - 1026. S.-K. Kang, S.-W. Lee, M.-S. Kim, H.-S. Kwon, Synth. Commun. 2001, 31, 1721 - 1725. S.-K. Kang, T. Yamaguchi, T.-H. Kim, P.-S. Ho, J. Org. Chem. 1996, 61, 9082-9083.

  17. Suzuki Cross-Coupling Reaction Fast oxydative addition Electrophilic Palladium(II) S.-K. Kang, H.-W. Lee, S.-B. Jang, P.-S. Ho, J. Org. Chem. 1996, 61, 4720-4724.

  18. Pd Catalyzed C-H Functionalization

  19. Cyclopalladation Mechanisms O. Daugulis, V. G. Zaitsev, Angew. Chem., Int. Ed. 2005, 44, 4046-4048.

  20. Electrophilic Palladation Mechanisms O. Daugulis, V. G. Zaitsev, Angew. Chem., Int. Ed. 2005, 44, 4046-4048.

  21. Zaitsev O. Daugulis, V. G. Zaitsev, Angew. Chem., Int. Ed. 2005, 44, 4046-4048.

  22. Zaitsev O. Daugulis, V. G. Zaitsev, Angew. Chem., Int. Ed. 2005, 44, 4046-4048.

  23. Zaitsev Reaction faster with Ar-I containing electron-donating groups Reaction is faster with anilides containing electron-donating groups O. Daugulis, V. G. Zaitsev, Angew. Chem., Int. Ed. 2005, 44, 4046-4048.

  24. Mechanism ? O. Daugulis, V. G. Zaitsev, Angew. Chem., Int. Ed. 2005, 44, 4046-4048.

  25. Sanford D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330-7331.

  26. Sanford D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330-7331.

  27. Sanford D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330-7331.

  28. Mechanism ? Reaction does not work with Ph-I or PhOTf D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330-7331.

  29. Mechanism ? D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330-7331.

  30. Sanford N. R. Deprez, D. Kalyani, A. Krause, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 4972-4973.

  31. Sanford N. R. Deprez, D. Kalyani, A. Krause, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 4972-4973.

  32. Sanford N. R. Deprez, D. Kalyani, A. Krause, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 4972-4973.

  33. Ritter D. C. Powers, M. A. L. Geibel, J. E. M. N. Klein, T. Ritter, J. Am. Chem. Soc. 2009, ASAP.

  34. Ritter D. C. Powers, M. A. L. Geibel, J. E. M. N. Klein, T. Ritter, J. Am. Chem. Soc. 2009, ASAP.

  35. Cu Catalyzed C-H Functionalization

  36. Gaunt R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172-8174.

  37. Gaunt R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172-8174.

  38. Gaunt R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172-8174.

  39. Gaunt R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172-8174.

  40. Gaunt R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172-8174.

  41. Gaunt R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172-8174.

  42. Gaunt R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593-1597.

  43. Gaunt R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593-1597.

  44. Gaunt

  45. Synthesis

  46. Synthesis M. Bielawski, M. Zhu, B. Olofsson, Adv. Synth. Catal. 2007, 349, 2610-2618. M. Bielawski, B. Olofsson, Chem. Commun. 2007, 2521-2523.

  47. Synthesis M. Bielawski, M. Zhu, B. Olofsson, Adv. Synth. Catal. 2007, 349, 2610-2618. M. Bielawski, B. Olofsson, Chem. Commun. 2007, 2521-2523.

  48. Synthesis E. A. Merritt, J. Malmgren, F. J. Klinke, B. Olofsson, Synlett 2009, 2009, 2277-2280. M. Zhu, N. Jalalian, B. Olofsson, Synlett 2008, 592-596.

  49. Conclusion Diaryliodonium salts: Cross-Coupling Pd Catalyzed C-H Functionalization Pd Catalyzed C-H Functionalization Synthesis

  50. Thanks

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