Highly regioselective oxygenation of C-H bonds: Diamidomanganese constructs with attached substrates as catalyst models

Angewandte Chemie - International Edition

Volumn 39, Issue 9, 2000, Pages 1618-1621

  Moreira, Rayane F ^a   Wehn, Paul M ^a   Sames, Dalibor ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

C H activation; Manganese; N ligands; Oxygen transfer

Indexed keywords

CARBON; HYDROGEN; LIGAND; MANGANESE; METAL COMPLEX; NITROGEN;

ARTICLE; CATALYST; COVALENT BOND; MODEL; OXIDATION; OXYGEN TRANSPORT; OXYGENATION; STEREOCHEMISTRY;

EID: 0034595393     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000502)39:9<1618::AID-ANIE1618>3.0.CO;2-M     Document Type: Article

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30. M. Havranek, A. Singh, D. Sames, J. Am. Chem. Soc. 1999, 121, 8965-8966. See also M. B. Francis, E. M. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941. For recent combinatorial approaches to catalysis: A. H. Hoveyda, Chem. Biol. 1998, 5, R187-R191; B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. 1998, 110, 2788-2792; Angew. Chem. Int. Ed. 1998, 37, 2644-2647; M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650; D. Moye-Sherman, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1998, 2377-2378; A. Porte, J. Reibenspies, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180-9187; K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132; A. Berkessel, D. A. Herault, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105; H. Joo, Z. Lin, F. H. Arnold, Nature 1999, 399, 670-673.
31. M. Havranek, A. Singh, D. Sames, J. Am. Chem. Soc. 1999, 121, 8965-8966. See also M. B. Francis, E. M. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941. For recent combinatorial approaches to catalysis: A. H. Hoveyda, Chem. Biol. 1998, 5, R187-R191; B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. 1998, 110, 2788-2792; Angew. Chem. Int. Ed. 1998, 37, 2644-2647; M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650; D. Moye-Sherman, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1998, 2377-2378; A. Porte, J. Reibenspies, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180-9187; K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132; A. Berkessel, D. A. Herault, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105; H. Joo, Z. Lin, F. H. Arnold, Nature 1999, 399, 670-673.
32. M. Havranek, A. Singh, D. Sames, J. Am. Chem. Soc. 1999, 121, 8965-8966. See also M. B. Francis, E. M. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941. For recent combinatorial approaches to catalysis: A. H. Hoveyda, Chem. Biol. 1998, 5, R187-R191; B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. 1998, 110, 2788-2792; Angew. Chem. Int. Ed. 1998, 37, 2644-2647; M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650; D. Moye-Sherman, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1998, 2377-2378; A. Porte, J. Reibenspies, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180-9187; K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132; A. Berkessel, D. A. Herault, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105; H. Joo, Z. Lin, F. H. Arnold, Nature 1999, 399, 670-673.
33. M. Havranek, A. Singh, D. Sames, J. Am. Chem. Soc. 1999, 121, 8965-8966. See also M. B. Francis, E. M. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941. For recent combinatorial approaches to catalysis: A. H. Hoveyda, Chem. Biol. 1998, 5, R187-R191; B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. 1998, 110, 2788-2792; Angew. Chem. Int. Ed. 1998, 37, 2644-2647; M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650; D. Moye-Sherman, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1998, 2377-2378; A. Porte, J. Reibenspies, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180-9187; K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132; A. Berkessel, D. A. Herault, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105; H. Joo, Z. Lin, F. H. Arnold, Nature 1999, 399, 670-673.
34. M. Havranek, A. Singh, D. Sames, J. Am. Chem. Soc. 1999, 121, 8965-8966. See also M. B. Francis, E. M. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941. For recent combinatorial approaches to catalysis: A. H. Hoveyda, Chem. Biol. 1998, 5, R187-R191; B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. 1998, 110, 2788-2792; Angew. Chem. Int. Ed. 1998, 37, 2644-2647; M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650; D. Moye-Sherman, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1998, 2377-2378; A. Porte, J. Reibenspies, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180-9187; K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132; A. Berkessel, D. A. Herault, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105; H. Joo, Z. Lin, F. H. Arnold, Nature 1999, 399, 670-673.
35. M. Havranek, A. Singh, D. Sames, J. Am. Chem. Soc. 1999, 121, 8965-8966. See also M. B. Francis, E. M. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941. For recent combinatorial approaches to catalysis: A. H. Hoveyda, Chem. Biol. 1998, 5, R187-R191; B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. 1998, 110, 2788-2792; Angew. Chem. Int. Ed. 1998, 37, 2644-2647; M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650; D. Moye-Sherman, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1998, 2377-2378; A. Porte, J. Reibenspies, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180-9187; K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132; A. Berkessel, D. A. Herault, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105; H. Joo, Z. Lin, F. H. Arnold, Nature 1999, 399, 670-673.
36. M. Havranek, A. Singh, D. Sames, J. Am. Chem. Soc. 1999, 121, 8965-8966. See also M. B. Francis, E. M. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941. For recent combinatorial approaches to catalysis: A. H. Hoveyda, Chem. Biol. 1998, 5, R187-R191; B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. 1998, 110, 2788-2792; Angew. Chem. Int. Ed. 1998, 37, 2644-2647; M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650; D. Moye-Sherman, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1998, 2377-2378; A. Porte, J. Reibenspies, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180-9187; K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132; A. Berkessel, D. A. Herault, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105; H. Joo, Z. Lin, F. H. Arnold, Nature 1999, 399, 670-673.
37. M. Havranek, A. Singh, D. Sames, J. Am. Chem. Soc. 1999, 121, 8965-8966. See also M. B. Francis, E. M. Jacobsen, Angew. Chem. 1999, 111, 987-991; Angew. Chem. Int. Ed. 1999, 38, 937-941. For recent combinatorial approaches to catalysis: A. H. Hoveyda, Chem. Biol. 1998, 5, R187-R191; B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648-2689; Angew. Chem. Int. Ed. 1999, 38, 2494-2532; M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902; A. Holzwarth, H.-W. Schmidt, W. F. Maier, Angew. Chem. 1998, 110, 2788-2792; Angew. Chem. Int. Ed. 1998, 37, 2644-2647; M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. 1998, 110, 2792-2795; Angew. Chem. Int. Ed. 1998, 37, 2647-2650; D. Moye-Sherman, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1998, 2377-2378; A. Porte, J. Reibenspies, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180-9187; K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132; A. Berkessel, D. A. Herault, Angew. Chem. 1999, 111, 99-102; Angew. Chem. Int. Ed. 1999, 38, 102-105; H. Joo, Z. Lin, F. H. Arnold, Nature 1999, 399, 670-673.
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45. Experimental protocols for synthesis and oxidation of complexes 1, 5, and 6 can be found in the Supporting information.
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