Nucleophilic additions of arylzinc compounds to aldehydes mediated by CrCl3: Efficient and facile synthesis of functionalized benzhydrols, 1(3H)- isobenzofuranones, benzyl alcohols, or diaryl ketones

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 1031-1036

  Ogawa, Yoshihiro ^a   Saiga, Akihiro ^a   Mori, Mitsuo ^a   Shibata, Takanori ^a   Takagi, Kentaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BENZOFURAN DERIVATIVE; BENZYL ALCOHOL; DIARYL KETONE; FURANONE DERIVATIVE; ZINC DERIVATIVE;

ANALYTIC METHOD; ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; ION TRANSPORT; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0034712164     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991444k     Document Type: Article

References (42)

1. For example, see: (a) Carruthers, W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982; Vol. 7, p 662. (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (c) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science: Oxford, 1995; Vol. 11, p 159.
2. For example, see: (a) Carruthers, W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982; Vol. 7, p 662. (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (c) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science: Oxford, 1995; Vol. 11, p 159.
3. For example, see: (a) Carruthers, W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982; Vol. 7, p 662. (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 211. (c) Knochel, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science: Oxford, 1995; Vol. 11, p 159.
4. For example, see: (a) Ochiai, H.; Nishihara, T.; Tamaru, Y.; Yoshida, Z. J. Org. Chem. 1988, 53, 1343. (b) Yeh, M. C. P.; Knochel, P.; Santa, L. E. Tetrahedron Lett. 1988, 29, 3887. (c) Gosmini, C.; Rollin, Y.; Gebehenne, C.; Lojou, E.; Ratovelomanana, V.; Perichon, J. Tetrahedron Lett. 1994, 35, 5637.
5. For example, see: (a) Ochiai, H.; Nishihara, T.; Tamaru, Y.; Yoshida, Z. J. Org. Chem. 1988, 53, 1343. (b) Yeh, M. C. P.; Knochel, P.; Santa, L. E. Tetrahedron Lett. 1988, 29, 3887. (c) Gosmini, C.; Rollin, Y.; Gebehenne, C.; Lojou, E.; Ratovelomanana, V.; Perichon, J. Tetrahedron Lett. 1994, 35, 5637.
6. For example, see: (a) Ochiai, H.; Nishihara, T.; Tamaru, Y.; Yoshida, Z. J. Org. Chem. 1988, 53, 1343. (b) Yeh, M. C. P.; Knochel, P.; Santa, L. E. Tetrahedron Lett. 1988, 29, 3887. (c) Gosmini, C.; Rollin, Y.; Gebehenne, C.; Lojou, E.; Ratovelomanana, V.; Perichon, J. Tetrahedron Lett. 1994, 35, 5637.
7. (a) Kondo, Y.; Takazawa, N.; Yamazaki, C.; Sakamoto, T. J. Org. Chem. 1994, 59, 4717.
8. (b) Kondo, Y.; Fujinami, M.; Uchiyama, M.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1997, 799.
9. (c) Berger, S.; Langer, F.; Lutz, C.; Knochel, P.; Mobley, T.; Reddy, C. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1496.
10. (d) Soai, K.; Kawase, Y.; Oshiro, A. J. Chem. Soc., Perkin Trans. 1 1991, 1613.
11. (e) Dosa, P.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445.
12. (f) Huang, W.-S.; Pu, L. J. Org. Chem. 1999, 64, 4222.
13. (a) Takagi, K.; Hayama, N.; Inokawa, S. Bull. Chem. Soc. Jpn. 1980, 53, 3691.
14. (b) Majid, T. N.; Knochel, P. Tetrahedron Lett. 1990, 31, 4413.
15. (c) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
16. (d) Takagi, K. Chem. Lett. 1993, 469.
17. (e) Okano, M.; Amano, M.; Takagi, K. Tetrahedron Lett. 1998, 39, 3001.
18. (a) Negishi, E.; Liu, F. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag GmbH: Weinheim, 1998; p 1.
19. (b) Erdik, E. Tetrahedron 1992, 48, 9577.
20. (c) Knochel, P.; Singer, D. R. Chem. Rev. 1993, 93, 2117.
21. (d) Knochel, P.; Almena, J. J.; Jones, P. Tetrahedron 1998, 54, 8275.
22. Preliminary communication: Ogawa, Y.; Mori, M.; Saiga, A.; Takagi, K. Chem. Lett. 1996, 1069.
23. For the reaction of alkoxychromium intermediates with TMSCl, see for example: Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533.
24. For the beneficial effect of TMSCl on enhancing the reactivities of aldehydes, see for example: (a) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (b) Tamaru, Y.; Nakamura, T.; Sakaguchi, M.; Ochiai, H.; Yoshida, Z. J. Chem. Soc., Chem. Commun. 1988, 610. (c) Gosmini, C.; Rollin, Y.; Gebehenne, C.; Lojou, E.; Ratovelomanana, V.; Perichon, J. Tetrahedron Lett. 1994, 35, 5637.
25. For the beneficial effect of TMSCl on enhancing the reactivities of aldehydes, see for example: (a) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (b) Tamaru, Y.; Nakamura, T.; Sakaguchi, M.; Ochiai, H.; Yoshida, Z. J. Chem. Soc., Chem. Commun. 1988, 610. (c) Gosmini, C.; Rollin, Y.; Gebehenne, C.; Lojou, E.; Ratovelomanana, V.; Perichon, J. Tetrahedron Lett. 1994, 35, 5637.
26. For the beneficial effect of TMSCl on enhancing the reactivities of aldehydes, see for example: (a) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (b) Tamaru, Y.; Nakamura, T.; Sakaguchi, M.; Ochiai, H.; Yoshida, Z. J. Chem. Soc., Chem. Commun. 1988, 610. (c) Gosmini, C.; Rollin, Y.; Gebehenne, C.; Lojou, E.; Ratovelomanana, V.; Perichon, J. Tetrahedron Lett. 1994, 35, 5637.
27. This result suggests that the alkoxychromium intermediate does not undergo the spontaneous β-elimination reaction under the reaction conditions. However, see also: Ito, T.; Ono, T.; Maruyama, K.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1982, 55, 2212.
28. 3]ZnX, or others.
29. 11b,c (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (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) Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Chen, D.; Takai, K.; Ochiai, M. Tetrahedron Lett. 1997, 38, 8211.
30. 11b,c (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (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) Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Chen, D.; Takai, K.; Ochiai, M. Tetrahedron Lett. 1997, 38, 8211.
31. 11b,c (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (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) Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Chen, D.; Takai, K.; Ochiai, M. Tetrahedron Lett. 1997, 38, 8211.
32. 11b,c (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (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) Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Chen, D.; Takai, K.; Ochiai, M. Tetrahedron Lett. 1997, 38, 8211.
33. 11b,c (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (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) Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Chen, D.; Takai, K.; Ochiai, M. Tetrahedron Lett. 1997, 38, 8211.
34. 11b,c (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (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) Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Chen, D.; Takai, K.; Ochiai, M. Tetrahedron Lett. 1997, 38, 8211.
35. 3+-mediated addition of organometallic compounds to aldehydes, see (a) Saccomano, N. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 173. (b) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 386.
36. 3+-mediated addition of organometallic compounds to aldehydes, see (a) Saccomano, N. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 173. (b) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 386.
37. Kirtley, S. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982; Vol. 3, p 783.
38. Renson, M. Bull. Soc. Chim. Belges. 1961, 70, 77.
39. Lund, H. J. Chem. Soc. 1928, 1569.
40. Tasman, A. Rec. Trav. Chim. 1927, 46, 653.
41. Smith, J. G.; Wikman, R. T. Tetrahedron 1974, 30, 2603.
42. Berti, G.; Marsili, A.; Mini, V. Ann. Chim. 1960, 50, 669.