Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 169-175

  Bolm, Carsten ^a   Hildebrand, Jens P ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; IODINE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; MOLECULAR INTERACTION; PROTEIN STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033977363     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991342u     Document Type: Article

References (70)

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7. For some recent examples see: (a) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (b) Reggelin, M.; Heinrich, T. Angew. Chem. 1998, 110, 3005; Angew. Chem., Int. Ed. 1998, 37, 2883. (c) Bosshammer, S.; Gais, H.-J. Synthesis 1998, 919. (d) For a recent application of sulfoximines in natural product synthesis see: Paquette, L. A.; Gao, Z.; Ni, Z.; Smith, G. F. J. Am. Chem. Soc. 1998, 120, 2543. (e) For the synthesis of benzothiazines containing the sulfonimidoyl fragment see: Harmata, M.; Kahraman, M.; Jones, D. E.; Pavri, N.; Weatherwax, S. E. Tetrahedron 1998, 54, 9995.
8. For some recent examples see: (a) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (b) Reggelin, M.; Heinrich, T. Angew. Chem. 1998, 110, 3005; Angew. Chem., Int. Ed. 1998, 37, 2883. (c) Bosshammer, S.; Gais, H.-J. Synthesis 1998, 919. (d) For a recent application of sulfoximines in natural product synthesis see: Paquette, L. A.; Gao, Z.; Ni, Z.; Smith, G. F. J. Am. Chem. Soc. 1998, 120, 2543. (e) For the synthesis of benzothiazines containing the sulfonimidoyl fragment see: Harmata, M.; Kahraman, M.; Jones, D. E.; Pavri, N.; Weatherwax, S. E. Tetrahedron 1998, 54, 9995.
9. For some recent examples see: (a) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (b) Reggelin, M.; Heinrich, T. Angew. Chem. 1998, 110, 3005; Angew. Chem., Int. Ed. 1998, 37, 2883. (c) Bosshammer, S.; Gais, H.-J. Synthesis 1998, 919. (d) For a recent application of sulfoximines in natural product synthesis see: Paquette, L. A.; Gao, Z.; Ni, Z.; Smith, G. F. J. Am. Chem. Soc. 1998, 120, 2543. (e) For the synthesis of benzothiazines containing the sulfonimidoyl fragment see: Harmata, M.; Kahraman, M.; Jones, D. E.; Pavri, N.; Weatherwax, S. E. Tetrahedron 1998, 54, 9995.
10. For some recent examples see: (a) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (b) Reggelin, M.; Heinrich, T. Angew. Chem. 1998, 110, 3005; Angew. Chem., Int. Ed. 1998, 37, 2883. (c) Bosshammer, S.; Gais, H.-J. Synthesis 1998, 919. (d) For a recent application of sulfoximines in natural product synthesis see: Paquette, L. A.; Gao, Z.; Ni, Z.; Smith, G. F. J. Am. Chem. Soc. 1998, 120, 2543. (e) For the synthesis of benzothiazines containing the sulfonimidoyl fragment see: Harmata, M.; Kahraman, M.; Jones, D. E.; Pavri, N.; Weatherwax, S. E. Tetrahedron 1998, 54, 9995.
11. For some recent examples see: (a) Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Org. Chem. 1997, 62, 2337. (b) Reggelin, M.; Heinrich, T. Angew. Chem. 1998, 110, 3005; Angew. Chem., Int. Ed. 1998, 37, 2883. (c) Bosshammer, S.; Gais, H.-J. Synthesis 1998, 919. (d) For a recent application of sulfoximines in natural product synthesis see: Paquette, L. A.; Gao, Z.; Ni, Z.; Smith, G. F. J. Am. Chem. Soc. 1998, 120, 2543. (e) For the synthesis of benzothiazines containing the sulfonimidoyl fragment see: Harmata, M.; Kahraman, M.; Jones, D. E.; Pavri, N.; Weatherwax, S. E. Tetrahedron 1998, 54, 9995.
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24. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
25. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
26. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
27. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
28. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
29. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
30. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
31. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
32. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
33. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
34. For the oxidation of N-aryl sulfimines to sulfoximines see: (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505. (b) Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 2510. For the synthesis of N-aryl sulfoximines with tert-butyl hypochlorite see: (c) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207. (d) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1. (e) Harmata, M. Tetrahedron Lett. 1989, 30, 437. (f) Harmata, M.; Claassen, R. J., II. Tetrahedron Lett. 1991, 32, 6497. For recent reviews see: (a) Hartwig, J. F. Synlett 1997, 329. (b) Hartwig, J. F. Angew. Chem. 1998, 110, 2154; Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (d) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287.
35. (e) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
36. (f) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
37. Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367.
38. (a) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
39. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
40. Bolm, C.; Hildebrand, J. P. Tetrahedron Lett. 1998, 39, 5731.
41. Racemic BINAP [2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] was used in all runs.
42. Tol-BINAP [2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl] was used either as the (S)- or the (R)-enantiomer; both gave identical results in the arylation reactions.
43. DPPF: 1,1′-(diphenylphosphino)ferrocene.
44. DPEphos: 2,2′-bis(diphenylphosphino)-1,1′-diphenyl ether. (a) For the synthesis of DPEphos see: Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K., Fraanje, J. Organometallics 1995, 14, 3081. For its use in related amination reactions see: (b) Sadighi, J. P.; Harris, M. C.; Buchwald, S. L. Tetrahedron Lett. 1998, 39, 5327. (c) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694.
45. DPEphos: 2,2′-bis(diphenylphosphino)-1,1′-diphenyl ether. (a) For the synthesis of DPEphos see: Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K., Fraanje, J. Organometallics 1995, 14, 3081. For its use in related amination reactions see: (b) Sadighi, J. P.; Harris, M. C.; Buchwald, S. L. Tetrahedron Lett. 1998, 39, 5327. (c) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694.
46. DPEphos: 2,2′-bis(diphenylphosphino)-1,1′-diphenyl ether. (a) For the synthesis of DPEphos see: Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K., Fraanje, J. Organometallics 1995, 14, 3081. For its use in related amination reactions see: (b) Sadighi, J. P.; Harris, M. C.; Buchwald, S. L. Tetrahedron Lett. 1998, 39, 5327. (c) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694.
47. 3 in organic synthesis see: Flessner, T.; Doye, S. J. Prakt. Chem. 1999, 341, 186.
48. On the other hand, DPEphos, which was among the best ligands for methyl 2-bromobenzoate (2), afforded (4-tert-butylphenyl)-S-methyl-S-phenylsulfoximine (9) in a disappointing yield of 23% under these modified conditions.
49. 3 as ligand in the synthesis of chiral arylamines. Racemization was avoided utilizing chelating ligands such as BINAP and DPPF: Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451.
50. Zhou, Q.-L.; Pfaltz, A. Tetrahedron 1994, 50, 4467.
51. 1H NMR shift experiments with 18 obtained from racemic and enantiomerically pure 3 provide further evidence that the coupling proceeds without racemization (see Supporting Information).
52. Bolm, C.; Bienewald, F.; Harms, K. Synlett 1996, 775.
53. (a) Louie, J.; Hartwig, J. F.; Fry, A. J. J. Am. Chem. Soc. 1997, 119, 11695.
54. (b) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367.
55. The separate reaction of isolated 22 with 3 did not result in the formation of bissulfoximine 23. While this article was under review, Harmata published a paper on the synthesis of chiral benzothiazines derived from 1,3- and 1,4-dibromobenzenes bearing additional formyl groups (see: Harmata, M.; Pavri, N. Angew. Chem. 1999, 111, 2577; Angew. Chem., Int. Ed. 1999, 38, 2419). Applying our protocol, they succeeded in substituting both bromines. However, the corresponding bissulfoximines were formed in only moderate yield.
56. The separate reaction of isolated 22 with 3 did not result in the formation of bissulfoximine 23. While this article was under review, Harmata published a paper on the synthesis of chiral benzothiazines derived from 1,3- and 1,4-dibromobenzenes bearing additional formyl groups (see: Harmata, M.; Pavri, N. Angew. Chem. 1999, 111, 2577; Angew. Chem., Int. Ed. 1999, 38, 2419). Applying our protocol, they succeeded in substituting both bromines. However, the corresponding bissulfoximines were formed in only moderate yield.
57. Bolm, C.; Hildebrand, J. P. Unpublished results.
58. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
59. (a) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
60. (b) Room-temperature arylation of amines with aryl iodides using crown ethers as additives: Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066.
61. (c) For room-temperature arylations of amines with aryl iodides using a highly reactive Pd catalyst see: Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
62. (d) Intramolecular amination with aryl iodides: Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525.
63. (e) For a high-yielding palladium-catalyzed reaction of an aryl iodide with diphenylhydrazone see: Hartwig, J. F. Angew. Chem. 1998, 110, 2249; Angew. Chem., Int. Ed. 1998, 37, 2090.
64. (e) For a high-yielding palladium- catalyzed reaction of an aryl iodide with diphenylhydrazone see: Hartwig, J. F. Angew. Chem. 1998, 110, 2249; Angew. Chem., Int. Ed. 1998, 37, 2090.
65. For an example of a copper(I)-catalyzed high-yielding arylation protocol of imidazoles see: Kiyomori, A.; Marcoux, J.-F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
66. 2(DPPF)/DPPF and 2 equiv of LiBr in THF afforded only 34% of coupled product.
67. No product derived from hydrodehalogenation (methyl benzoate) was observed as side product as determined by GC/MS.
68. This result is in contrast to Buchwald's protocol, which gives good to high yields with both electron-poor and electron-rich aryl iodides (ref 26b), and Hartwig reported that aniline can be coupled with 2-iodoanisole in 96% yield (ref 25).
69. Brandt, J.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 8, 909.
70. Furukawa, N.; Takahashi, F.; Yoshimura, T.; Oae, S. Tetrahedron 1979, 35, 317.