Chelation-induced catalytic multiple arylation of allylic 2-pyridyl sulfones

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1651-1654

  Llamas, Tomás ^a   Arrayás, Ramón Gómez ^a   Carretero, Juan Carlos ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Allylic substitution; Chelation induced; Copper; Heck reaction; Palladium; Pyridyl sulfone

Indexed keywords

2 PYRIDONE DERIVATIVE; ALLYL COMPOUND; SULFONE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHELATION; CHEMICAL REACTION; GRIGNARD REACTION; HECK REACTION; METAL BINDING; MOLECULAR INTERACTION; PHASE TRANSITION; REACTION ANALYSIS;

EID: 12344264766     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404180     Document Type: Article

References (48)

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17. For α,β-unsaturated sulfoxides, see: a) N. Diaz Buezo, I. Alonso, J. C. Carretero, J. Am. Chem. Soc. 1998, 120, 7129-7130; see also: b) N. Diaz Buezo, J. C. de la Rosa, J. Priego, I. Alonso, J. C. Carretero, Chem. Eur. J. 2001, 7, 3890-3900; for α,β-unsaturated sulfones, see: c) P. Mauleón, A. A. Núñez, I. Alonso, J. C. Carretero, Chem. Eur. J. 2003, 9, 1511-1520; d) P. Mauleón, I. Alonso, J. C. Carretero, Angew. Chem. Int. Ed. 2001, 40, 129 1-1293.
18. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
19. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
20. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
21. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
22. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
23. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
24. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
25. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
26. For recent examples on removable directing groups in other transition metal-catalyzed processes, see: a) P. Mauleón, J. C. Carretero, Org. Lett. 2004, 6, 3195-3198; b) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. Int. Ed. 2004, 43, 340-343; c) S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687-2690; d) D.-Y. Lee, B.-S. Hong, E.-G. Cho, H. Lee, C.-H. Jun, J. Am. Chem. Soc. 2003, 125, 6372-6373; e) K. Itami, M. Mineno, T. Kamei, J.-i. Yoshida, Org. Lett. 2002, 4, 3635-3638; d) S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751; f) C.-H. Jun, H. Lee, C. W. Moon, H.-S. Hong, J. Am. Chem. Soc. 2001, 123, 8600-8601; g) N. Chatani, H. Tatamidani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 4849-4850; h) B. Breit, Chem. Eur. J. 2000, 6, 1519-1524.
27. A similar synthetic approach has been reported for the preparation of related cyclic β,γ-unsaturated phenylsulfoximines, see: S. Koep, H.-J. Gais, G. Raabe, J. Am. Chem. Soc. 2003, 125, 13243-13251.
28. + in the Heck reaction, see: K. Karabelas, C. Westerlund, A. Hallberg, J. Org. Chem. 1985, 50, 3896-3900. Other suitable solvents of choice were DMA, NMP, while no reaction was observed in DMSO, toluene, DCE or 1,4-dioxane.
29. Reported yields refer to mixtures of mono- and diarylated compounds, which could not be separated by standard silica gel chromatography. Complete separation of both products can be achieved by further reverse phase silica gel chromatography (Merck, lichoprep RP-18, 40-63 μm), pure compounds 6-10 being isolated in 50-60% overall yields.
30. In this particular case, the use of aryldiazonium salts did not improve the reactivity.
31. For a review on transition metal-catalyzed C-C bond formation with Grignard reagents, see: H. Shinokubo, K. Oshima, Eur. J. Org. Chem. 2004, 2081-2091.
32. For a recent report on Cu-mediated allylic substitution using a coordinating leaving group, see: a) B. Breit, P. Demel, C. Studte, Angew. Chem. Int. Ed. 2004, 43, 2-5; for copper-mediated alkylation of allylic sulfoximines, see: b) M. Scommoda, H.-J. Gais, S. Bosshammer, G. Raabe, J. Org. Chem. 1996, 61, 4379-4390; c) H.-J. Gais, H. Müller, J. Bund, M. Scommoda, J. Brandt, G. Raabe, J. Am. Chem. Soc. 1995, 117, 2453-2466.
33. For a recent report on Cu-mediated allylic substitution using a coordinating leaving group, see: a) B. Breit, P. Demel, C. Studte, Angew. Chem. Int. Ed. 2004, 43, 2-5; for copper-mediated alkylation of allylic sulfoximines, see: b) M. Scommoda, H.-J. Gais, S. Bosshammer, G. Raabe, J. Org. Chem. 1996, 61, 4379-4390; c) H.-J. Gais, H. Müller, J. Bund, M. Scommoda, J. Brandt, G. Raabe, J. Am. Chem. Soc. 1995, 117, 2453-2466.
34. For a recent report on Cu-mediated allylic substitution using a coordinating leaving group, see: a) B. Breit, P. Demel, C. Studte, Angew. Chem. Int. Ed. 2004, 43, 2-5; for copper-mediated alkylation of allylic sulfoximines, see: b) M. Scommoda, H.-J. Gais, S. Bosshammer, G. Raabe, J. Org. Chem. 1996, 61, 4379-4390; c) H.-J. Gais, H. Müller, J. Bund, M. Scommoda, J. Brandt, G. Raabe, J. Am. Chem. Soc. 1995, 117, 2453-2466.
35. For recent examples on copper-catalyzed processes, see: a) A. W. Van Zijl, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413-420; b) A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147-4149; c) A. S. E. Karlström, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 1981-1989; d) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927-930; e) A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar, J.-E. Bäckvall, Synlett 2001, 923-926; f) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456-1460; g) H. Malda, A. W. Van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171.
36. For recent examples on copper-catalyzed processes, see: a) A. W. Van Zijl, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413-420; b) A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147-4149; c) A. S. E. Karlström, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 1981-1989; d) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927-930; e) A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar, J.-E. Bäckvall, Synlett 2001, 923-926; f) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456-1460; g) H. Malda, A. W. Van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171.
37. For recent examples on copper-catalyzed processes, see: a) A. W. Van Zijl, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413-420; b) A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147-4149; c) A. S. E. Karlström, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 1981-1989; d) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927-930; e) A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar, J.-E. Bäckvall, Synlett 2001, 923-926; f) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456-1460; g) H. Malda, A. W. Van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171.
38. For recent examples on copper-catalyzed processes, see: a) A. W. Van Zijl, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413-420; b) A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147-4149; c) A. S. E. Karlström, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 1981-1989; d) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927-930; e) A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar, J.-E. Bäckvall, Synlett 2001, 923-926; f) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456-1460; g) H. Malda, A. W. Van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171.
39. For recent examples on copper-catalyzed processes, see: a) A. W. Van Zijl, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413-420; b) A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147-4149; c) A. S. E. Karlström, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 1981-1989; d) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927-930; e) A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar, J.-E. Bäckvall, Synlett 2001, 923-926; f) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456-1460; g) H. Malda, A. W. Van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171.
40. For recent examples on copper-catalyzed processes, see: a) A. W. Van Zijl, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413-420; b) A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147-4149; c) A. S. E. Karlström, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 1981-1989; d) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927-930; e) A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar, J.-E. Bäckvall, Synlett 2001, 923-926; f) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456-1460; g) H. Malda, A. W. Van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171.
41. For recent examples on copper-catalyzed processes, see: a) A. W. Van Zijl, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413-420; b) A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147-4149; c) A. S. E. Karlström, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 1981-1989; d) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927-930; e) A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar, J.-E. Bäckvall, Synlett 2001, 923-926; f) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456-1460; g) H. Malda, A. W. Van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171.
42. a) B. M. Trost, C. A. Merlic, J. Am. Chem. Soc. 1988, 110, 5216-5218;
43. b) M. Julia, A. Righini, J.-N. Verpeaux, Tetrahedron Lett. 1919, 20, 2393-2396; M. Julia, A. Righini, J.-N. Verpeaux, Tetrahedron 1983, 39, 3283-3287.
44. b) M. Julia, A. Righini, J.-N. Verpeaux, Tetrahedron Lett. 1919, 20, 2393-2396; M. Julia, A. Righini, J.-N. Verpeaux, Tetrahedron 1983, 39, 3283-3287.
45. The dramatic rate acceleration effect observed in these copper-catalyzed allylic substitutions could also be due to the better leaving group nature of the 2-pyridylsulfonyl group compared to the typical phenylsulfonyl group. Investigation directed towards differentiate between chelation or electronic assistance is currently under progress.
46. CuTC = copper thiophene-2-carboxylate: G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748-2749.
47. 2 proved to be the most suitable for the reaction, while diethyl ether or toluene provided very low conversions.
48. For general remarks, see: O. García Mancheño, J. Priego, S. Cabrera, R. Gómez Arrayás, T. Llamas, J. C. Carretero, J. Org. Chem. 2003, 68, 3679-3686.