Samarium iodide-catalyzed pinacol coupling of carbonyl compounds

Journal of the American Chemical Society

Volumn 118, Issue 46, 1996, Pages 11666-11667

  Nomura, Ryoji ^a   Matsuno, Tatsuya ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029955479     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962331a     Document Type: Article

References (45)

1. For recent reviews for the application of low-valent samarium compounds into organic chemistry, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, Great Britain, 1994. (c) Molander, G. A. Chem. Rev. 1992, 92, 29. (d) Molander, G. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Great Britain, 1991; Vol. 1, Chapter 9, p 251. (e) Inanaga, J. Yuki Gosei Kagaku Kyokaishi 1989, 47, 200. (f) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (g) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, Jr., K. A., Eyring, L., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1984; Vol. 6, Chapter 50, p 525.
2. For recent reviews for the application of low-valent samarium compounds into organic chemistry, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, Great Britain, 1994. (c) Molander, G. A. Chem. Rev. 1992, 92, 29. (d) Molander, G. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Great Britain, 1991; Vol. 1, Chapter 9, p 251. (e) Inanaga, J. Yuki Gosei Kagaku Kyokaishi 1989, 47, 200. (f) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (g) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, Jr., K. A., Eyring, L., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1984; Vol. 6, Chapter 50, p 525.
3. For recent reviews for the application of low-valent samarium compounds into organic chemistry, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, Great Britain, 1994. (c) Molander, G. A. Chem. Rev. 1992, 92, 29. (d) Molander, G. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Great Britain, 1991; Vol. 1, Chapter 9, p 251. (e) Inanaga, J. Yuki Gosei Kagaku Kyokaishi 1989, 47, 200. (f) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (g) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, Jr., K. A., Eyring, L., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1984; Vol. 6, Chapter 50, p 525.
4. For recent reviews for the application of low-valent samarium compounds into organic chemistry, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, Great Britain, 1994. (c) Molander, G. A. Chem. Rev. 1992, 92, 29. (d) Molander, G. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Great Britain, 1991; Vol. 1, Chapter 9, p 251. (e) Inanaga, J. Yuki Gosei Kagaku Kyokaishi 1989, 47, 200. (f) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (g) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, Jr., K. A., Eyring, L., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1984; Vol. 6, Chapter 50, p 525.
5. For recent reviews for the application of low-valent samarium compounds into organic chemistry, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, Great Britain, 1994. (c) Molander, G. A. Chem. Rev. 1992, 92, 29. (d) Molander, G. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Great Britain, 1991; Vol. 1, Chapter 9, p 251. (e) Inanaga, J. Yuki Gosei Kagaku Kyokaishi 1989, 47, 200. (f) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (g) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, Jr., K. A., Eyring, L., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1984; Vol. 6, Chapter 50, p 525.
6. For recent reviews for the application of low-valent samarium compounds into organic chemistry, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, Great Britain, 1994. (c) Molander, G. A. Chem. Rev. 1992, 92, 29. (d) Molander, G. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Great Britain, 1991; Vol. 1, Chapter 9, p 251. (e) Inanaga, J. Yuki Gosei Kagaku Kyokaishi 1989, 47, 200. (f) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (g) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, Jr., K. A., Eyring, L., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1984; Vol. 6, Chapter 50, p 525.
7. For recent reviews for the application of low-valent samarium compounds into organic chemistry, see: (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (b) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, Great Britain, 1994. (c) Molander, G. A. Chem. Rev. 1992, 92, 29. (d) Molander, G. A. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Great Britain, 1991; Vol. 1, Chapter 9, p 251. (e) Inanaga, J. Yuki Gosei Kagaku Kyokaishi 1989, 47, 200. (f) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (g) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gschneidner, Jr., K. A., Eyring, L., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1984; Vol. 6, Chapter 50, p 525.
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16. 3-associated electroreductions were reported although it appears to be difficult to conclude that electrochemically formed Sm(II) species work as reducing agents. See: (a) Hébri, H.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1993, 499. (b) Espanet, B.; Duñach, E.; Périchon, J. Tetrahedron Lett. 1992, 33, 2485. (c) Hébri, H.; Duñach, E.; Périchon, J. Synlett 1992, 293. (d) Hébri, H.; Duñach, E.; Périchon, J. Syn. Commun. 1991, 21, 2377. (e) Hébri, H.; Duñach, E.; Heintz, M.; Troupel, M.; Périchon, J. Synlett 1991, 901. (f) Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1989, 276.
17. 3-associated electroreductions were reported although it appears to be difficult to conclude that electrochemically formed Sm(II) species work as reducing agents. See: (a) Hébri, H.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1993, 499. (b) Espanet, B.; Duñach, E.; Périchon, J. Tetrahedron Lett. 1992, 33, 2485. (c) Hébri, H.; Duñach, E.; Périchon, J. Synlett 1992, 293. (d) Hébri, H.; Duñach, E.; Périchon, J. Syn. Commun. 1991, 21, 2377. (e) Hébri, H.; Duñach, E.; Heintz, M.; Troupel, M.; Périchon, J. Synlett 1991, 901. (f) Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1989, 276.
18. 3-associated electroreductions were reported although it appears to be difficult to conclude that electrochemically formed Sm(II) species work as reducing agents. See: (a) Hébri, H.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1993, 499. (b) Espanet, B.; Duñach, E.; Périchon, J. Tetrahedron Lett. 1992, 33, 2485. (c) Hébri, H.; Duñach, E.; Périchon, J. Synlett 1992, 293. (d) Hébri, H.; Duñach, E.; Périchon, J. Syn. Commun. 1991, 21, 2377. (e) Hébri, H.; Duñach, E.; Heintz, M.; Troupel, M.; Périchon, J. Synlett 1991, 901. (f) Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1989, 276.
19. 3-associated electroreductions were reported although it appears to be difficult to conclude that electrochemically formed Sm(II) species work as reducing agents. See: (a) Hébri, H.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1993, 499. (b) Espanet, B.; Duñach, E.; Périchon, J. Tetrahedron Lett. 1992, 33, 2485. (c) Hébri, H.; Duñach, E.; Périchon, J. Synlett 1992, 293. (d) Hébri, H.; Duñach, E.; Périchon, J. Syn. Commun. 1991, 21, 2377. (e) Hébri, H.; Duñach, E.; Heintz, M.; Troupel, M.; Périchon, J. Synlett 1991, 901. (f) Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1989, 276.
20. 3-associated electroreductions were reported although it appears to be difficult to conclude that electrochemically formed Sm(II) species work as reducing agents. See: (a) Hébri, H.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1993, 499. (b) Espanet, B.; Duñach, E.; Périchon, J. Tetrahedron Lett. 1992, 33, 2485. (c) Hébri, H.; Duñach, E.; Périchon, J. Synlett 1992, 293. (d) Hébri, H.; Duñach, E.; Périchon, J. Syn. Commun. 1991, 21, 2377. (e) Hébri, H.; Duñach, E.; Heintz, M.; Troupel, M.; Périchon, J. Synlett 1991, 901. (f) Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1989, 276.
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26. 2 and excess of Mg although any further investigation was not performed. See, ref 5e.
27. 2 was not determined in this experiment.
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29. 2-mediated pinacol coupling, see: (a) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765. (b) Souppe, J.; Danon, L.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1983, 250, 227. (c) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (d) Shiue, J. S.; Lin, C. C.; Fang, J. M. Tetrahedron Lett. 1993, 34, 335. (e) Okaue, Y.; Isobe, T. Mem. Fac. Sci., Kyushu Univ., Ser. C 1992, 18, 179.
30. 2-mediated pinacol coupling, see: (a) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765. (b) Souppe, J.; Danon, L.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1983, 250, 227. (c) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (d) Shiue, J. S.; Lin, C. C.; Fang, J. M. Tetrahedron Lett. 1993, 34, 335. (e) Okaue, Y.; Isobe, T. Mem. Fac. Sci., Kyushu Univ., Ser. C 1992, 18, 179.
31. 2-mediated pinacol coupling, see: (a) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765. (b) Souppe, J.; Danon, L.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1983, 250, 227. (c) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (d) Shiue, J. S.; Lin, C. C.; Fang, J. M. Tetrahedron Lett. 1993, 34, 335. (e) Okaue, Y.; Isobe, T. Mem. Fac. Sci., Kyushu Univ., Ser. C 1992, 18, 179.
32. 2-mediated pinacol coupling, see: (a) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765. (b) Souppe, J.; Danon, L.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1983, 250, 227. (c) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (d) Shiue, J. S.; Lin, C. C.; Fang, J. M. Tetrahedron Lett. 1993, 34, 335. (e) Okaue, Y.; Isobe, T. Mem. Fac. Sci., Kyushu Univ., Ser. C 1992, 18, 179.
33. 2-mediated pinacol coupling, see: (a) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765. (b) Souppe, J.; Danon, L.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1983, 250, 227. (c) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (d) Shiue, J. S.; Lin, C. C.; Fang, J. M. Tetrahedron Lett. 1993, 34, 335. (e) Okaue, Y.; Isobe, T. Mem. Fac. Sci., Kyushu Univ., Ser. C 1992, 18, 179.
34. For examples of Mg-promoted pinacol coupling reactions, see: (a) Rausch, M. D.; McEwen, W. E.; Kleinberg, J. Chem. Rev. 1957, 57, 417. (b) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (c) Csuk, R.; Fürstner, A.; Weidmann, H. J. Chem. Soc., Chem. Commun. 1986, 1802. (d) Adams, R.; Adams, E. W. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. I. p 459.
35. For examples of Mg-promoted pinacol coupling reactions, see: (a) Rausch, M. D.; McEwen, W. E.; Kleinberg, J. Chem. Rev. 1957, 57, 417. (b) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (c) Csuk, R.; Fürstner, A.; Weidmann, H. J. Chem. Soc., Chem. Commun. 1986, 1802. (d) Adams, R.; Adams, E. W. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. I. p 459.
36. For examples of Mg-promoted pinacol coupling reactions, see: (a) Rausch, M. D.; McEwen, W. E.; Kleinberg, J. Chem. Rev. 1957, 57, 417. (b) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (c) Csuk, R.; Fürstner, A.; Weidmann, H. J. Chem. Soc., Chem. Commun. 1986, 1802. (d) Adams, R.; Adams, E. W. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. I. p 459.
37. For examples of Mg-promoted pinacol coupling reactions, see: (a) Rausch, M. D.; McEwen, W. E.; Kleinberg, J. Chem. Rev. 1957, 57, 417. (b) Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729. (c) Csuk, R.; Fürstner, A.; Weidmann, H. J. Chem. Soc., Chem. Commun. 1986, 1802. (d) Adams, R.; Adams, E. W. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. I. p 459.
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41. 2 column chromatography) gave the mixture (dl and mesa) of pinacols.
42. The stoichiometric reaction gave 4-iodobutyl trimethylsilyl ether as a byproduct, whereas it was not detected in the catalytic reaction.
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