A "Hard/Soft" Mismatch Enables Catalytic Friedel-Crafts Acylations

Organic Letters

Volumn 3, Issue 3, 2001, Pages 417-420

  Fürstner, Alois ^a   Voigtländer, David ^a   Schrader, Wolfgang ^a   Giebel, Dirk ^a   Reetz, Manfred T ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

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ARTICLE;

EID: 0001057028     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0069251     Document Type: Article

References (66)

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24. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
25. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
26. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
27. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
28. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
29. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
30. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
31. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
32. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
33. For further methods, see: (a) Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379. (b) Effenberger, F.; Epple, G. Angew. Chem. 1972, 84, 295. (c) Effenberger, F.; Sohn, E.; Epple, G. Chem. Ber. 1983, 116, 1195. (d) Effenberger, F.; Steegmuller, D. Chem. Ber. 1988, 121, 117. (e) Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1994, 1703. (f) Pearson, D. E.; Buehler, C. A. Synthesis 1972, 533. (g) Hino, M.; Arata, K. Chem. Lett. 1978, 325. (h) Nomiya, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089. (i) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229. (j) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem. 1986, 51, 2128.
34. For previous studies from this laboratory on the evolution of transition metal promoted transformations into catalytic processes, see: (a) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468. (b) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533. (c) Fürstner A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349. (d) Fürstner, A. Chem. Eur. J. 1998, 4, 567.
35. For previous studies from this laboratory on the evolution of transition metal promoted transformations into catalytic processes, see: (a) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468. (b) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533. (c) Fürstner A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349. (d) Fürstner, A. Chem. Eur. J. 1998, 4, 567.
36. For previous studies from this laboratory on the evolution of transition metal promoted transformations into catalytic processes, see: (a) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468. (b) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533. (c) Fürstner A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349. (d) Fürstner, A. Chem. Eur. J. 1998, 4, 567.
37. For previous studies from this laboratory on the evolution of transition metal promoted transformations into catalytic processes, see: (a) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468. (b) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533. (c) Fürstner A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349. (d) Fürstner, A. Chem. Eur. J. 1998, 4, 567.
38. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
39. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
40. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
41. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
42. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
43. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
44. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
45. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
46. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
47. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
48. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
49. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
50. For previous applications of cationic Pd(II) or Pt(II) complexes in synthesis, see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Kataoka, Y.; Matsumoto, O.; Ohashi, M.; Yamagata, T.; Tani, K. Chem. Lett. 1994, 1283. (c) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660. (e) Nieddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Tetrahedron Lett. 1999, 40, 6987. (f) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253. (g) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (h) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (i) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648. (j) Cataldo, M.; Nieddu, E.; Gavagnin, R.; Pinna, F.; Strukul, G. J. Mol. Catal. A: Chem. 1999, 142, 305. (k) Gorla, F.; Venanzi, L. M. Helv. Chim. Acta 1990, 73, 690. (l) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017. (m) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
51. (a) Fürstner, A.; Szillat, H.; Gabon B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
52. (b) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785.
53. Fürstner, A.; Voigtländer, D. Synthesis 2000, 959.
54. 6) itself is not responsible for the observed catalytic activity in any of these cases.
55. 2 (63%), MeCN 13%), THF (0%).
56. Triflic acid is known to catalyze various FC acylations, cf. refs 5b, 5c, 5d, and literature cited therein.
57. Precipitated AgCl was filtered off under Ar prior to these spectroscopic investigations.
58. Note, however, that neutral Pt(II) triflate (trifluoroacetate) salts complexed by phosphines do not undergo electrophilic substitution of arenes, cf: (a) Brainard, R. L.; Null, W. R.; Lee, T. R.; Whitesides, G. M. Organometallics 1988, 7, 2379. (b) Peters, R. G.; White, S.; Roddick, D. M. Organometallics 1998, 17, 4493.
59. Note, however, that neutral Pt(II) triflate (trifluoroacetate) salts complexed by phosphines do not undergo electrophilic substitution of arenes, cf: (a) Brainard, R. L.; Null, W. R.; Lee, T. R.; Whitesides, G. M. Organometallics 1988, 7, 2379. (b) Peters, R. G.; White, S.; Roddick, D. M. Organometallics 1998, 17, 4493.
60. 3 has been shown to undergo reversible electrophilic substitution of arenes: Bisi Castellani, C.; Perotti, A.; Scrivanti, M.; Vidari, G. Tetrahedron 2000, 56, 8161.
61. 2 salts are known to induce electrophilic mercuration of arenes, cf.: (a) Olah, G. A.; Yu, S. H.; Parker, D. G. J. Org. Chem. 1976, 41, 1983. (b) Borovik, A. S.; Bott, S. G.; Barron, A. R. Angew. Chem., Int. Ed. 2000, 39, 4117.
62. 2 salts are known to induce electrophilic mercuration of arenes, cf.: (a) Olah, G. A.; Yu, S. H.; Parker, D. G. J. Org. Chem. 1976, 41, 1983. (b) Borovik, A. S.; Bott, S. G.; Barron, A. R. Angew. Chem., Int. Ed. 2000, 39, 4117.
63. The ESI MS spectra were recorded on an Ionspec Ultima high-resolution FT-MS spectrometer.
64. - are detected. MeOH used as the solvent for the ESI-MS experiments is the source of this additional ligand.
65. The assignments are unambiguous by (i) comparison of the experimentally observed isotope distribution patterns with the calculated ones and (ii) accurate mass determinations for the peaks of all individual platinum isotopes, cf. Figure 1.
66. 2O.