All-carbon quaternary centers via ruthenium-catalyzed hydroxymethylation of 2-substituted butadienes mediated by formaldehyde: Beyond hydroformylation

Journal of the American Chemical Society

Volumn 131, Issue 30, 2009, Pages 10366-10367

  Smejkal, Tomas ^a,b   Han, Hoon ^b   Breit, Bernhard ^a   Krische, Michael J ^a,b  

^a UNIVERSITY OF FREIBURG   (Germany)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-PROPANOL; C-C COUPLING; CATALYTIC MECHANISMS; CATALYTIC SYSTEM; CHEMICAL EQUATIONS; CONJUGATED DIENES; HYDROMETALATION; HYDROXYMETHYLATION; PARAFORMALDEHYDE; QUATERNARY CENTERS; REDUCTIVE COUPLINGS; REGIO-SELECTIVE; STANDARD CONDITIONS; TRANSFER HYDROGENATIONS;

ACETAL RESINS; BUTADIENE; HYDROFORMYLATION; HYDROXYLATION; RUTHENIUM;

ORGANIC POLYMERS;

1,3 BUTADIENE; CARBON; FORMALDEHYDE; RUTHENIUM;

ARTICLE; CATALYSIS; COUPLING FACTOR; CRYSTALLIZATION; HYDROFORMYLATION; HYDROGENATION; HYDROXYLATION; ISOMERIZATION; ISOTOPE LABELING; METHYLATION; MOLECULAR MECHANICS; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION;

BUTADIENES; CARBON; CATALYSIS; FORMALDEHYDE; HYDROGENATION; ISOMERISM; METHYLATION; RUTHENIUM;

EID: 68049092152     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904124b     Document Type: Article

References (49)

1. For selected reviews on hydroformylation, see: (a) Weissermel, K.; Arpe, H.-J. Industrial OrganicChemistry; Wiley-VCH, Weinheim, Germany, 2003; pp 127-144.
2. (b) Rhodium Catalyzed Hydroformylation; van Leeuwen, P. W. N. M., Claver, C., Eds.; Kluwer: Dordrecht, The Netherlands, 2000.
3. (c) Breit, B.; Seiche, W. Synthesis 2001, 1.
4. Hydroformylation of conjugated dienes typically occurs in low yield to provide complex mixtures. See: (a) Clement, W. H.; Orchin, M. Ind. Eng. Chem. Prod. Res. Dev. 1965, 4, 283.
5. (b) Fell, B.; Bahrmann, H. J. Mol. Catal. 1977, 2, 211.
6. (c) Bahrmann, H.; Fell, B. J. Mol. Catal. 1980, 8, 329.
7. (d) Botteghi, C.; Branca, M.; Saba, A. J. Organomet. Chem. 1980, 184, C17.
8. (e) van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Mol. Catal. 1985, 31, 345.
9. (f) Chalchat, J. C.; Garry, R. P.; Lecomte, E.; Michet, A. Flavour Fragrance J. 1991, 6, 178.
10. (g) Bertozzi, S.; Campigli, N.; Vitulli, G.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1995, 487, 41.
11. (h) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155.
12. (i) Horiuchi, T.; Ohta, T.; Shirakawa, E.; Nozaki, K.; Takaya, H. Tetrahedron 1997, 53, 7795.
13. (j) Barros, H. J. V.; Hanson, B. E.; dos Santos, E. N.; Gusevskaya, E. V. Appl. Catal., A 2004, 278, 57.
14. (k) Barros, H. J. V.; da Silva, J. G.; Guimarães, C. C.; dos Santos, E. N.; Gusevskaya, E. V. Organometallics 2008, 27, 4523.
15. For selected reviews of C-C bond-forming hydrogenation and transfer hydrogenation, see: (a) Ngai, M.-Y.; Kong, J. R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
16. (b) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
17. (c) Bower, J. F.; Kim, I. S.; Patman, R. L.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 34.
18. For Ru-catalyzed C-C bond-forming transfer hydrogenation, see: Dienes: (a) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338.
19. (b) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120.
20. Allenes: (c) Ngai, M.-Y.; Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705.
21. (d) Skucas, E.; Zbieg, J. R.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 5054.
22. Alkynes: (e) Patman, R. L.; Chaulagain, M. R.; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066.
23. (f) Williams, V. M.; Leung, J. C.; Patman, R. L.; Krische, M. J. Tetrahedron 2009, 65, 5024.
24. Enynes: (g) Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem., Int. Ed. 2008, 47, 5220.
25. For related catalytic C-C couplings that occur by way of nucleophilic Ru π-allyls, see: (a) Tsuji, Y.; Mukai, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1989, 369, C51.
26. (b) Kondo, T.; Ono, H.; Satake, N.; Mitsudo, T.-a.; Watanabe, Y. Organometallics 1995, 14, 1945.
27. (c) Kondo, T.; Hiraishi, N.; Morisaki, Y.; Wada, K.; Watanabe, Y.; Mitsudo, T.-a. Organometallics 1998, 17, 2131.
28. (d) Yu, C.-M.; Lee, S.; Hong, Y.-T.; Yoon, S.-K. Tetrahedron Lett. 2004, 45, 6557.
29. (e) Omura, S.; Fukuyama, T.; Horiguchi, J.; Murakami, Y.; Ryu, I. J. Am. Chem. Soc. 2008, 130, 14094.
30. For selected reviews of Ru-catalyzed C-C coupling, see: (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
31. (b) Kondo, T.; Mitsudo, T.-a. Curr. Org. Chem. 2002, 6, 1163.
32. (c) Dérien, S.; Monnier, F.; Dixneuf, P. H. Top. Organomet. Chem. 2004, 11, 1.
33. For catalytic intermolecular diene-aldehyde reductive coupling, see: (a) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033.
34. (b) Takimoto, M.; Hiraga, Y.; Sato, Y.; Mori, M. Tetrahedron Lett. 1998, 39, 4543.
35. (c) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397.
36. (d) Kimura, M.; Shibata, K.; Koudahashi, Y.; Tamaru, Y. Tetrahedron Lett. 2000, 41, 6789.
37. (e) Kimura, M.; Ezoe, A.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. 2001, 40, 3600.
38. (f) Loh, T.-P.; Song, H.-Y.; Zhou, Y. Org. Lett. 2002, 4, 2715.
39. (g) Sato, Y.; Sawaki, R.; Saito, N.; Mori, M. J. Org. Chem. 2002, 67, 656.
40. (h) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 4074.
41. (i) Bareille, L.; Le Gendre, P.; Moïse, C. Chem. Commun. 2005, 775.
42. (j) Kimura, M.; Ezoe, A.; Mori, M.; Iwata, K.; Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 8559.
43. (k) Yang, Y.; Zhu, S.-F.; Duan, H.-F.; Zhou, C.-Y.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 2248.
44. (l) Sato, Y.; Hinata, Y.; Seki, R.; Oonishi, Y.; Saito, N. Org. Lett. 2007, 9, 5597.
45. For a recent review encompassing Ni-catalyzed diene-aldehyde reductive coupling, see: Kimuara, M.; Tamaru, Y. Top. Curr. Chem. 2007, 279, 173.
46. For isomerization of Ru π-allyls, see ref 5e and: Xue, P.; Bi, S.; Sung, H. H. Y.; Williams, I. D.; Lin, Z.; Jia, G. Organometallics 2004, 23, 4735.
47. Dobson, A.; Robinson, S. R.; Uttley, M. F. J. Chem. Soc., Dalton Trans. 1974, 370.
48. Optically enriched 3g was previously prepared in 10 steps via enzymatic resolution (see: Fadel, A.; Vandromme, L. Tetrahedron: Asymmetry 1999, 10, 1153. ). With the use of (R)-CatASium T2 as the ligand instead of dppb, optically enriched 3g (57% ee) is accessible in only two steps.
49. For a review of Ru-catalyzed alkene hydroformylation, see: Kalck, P.; Peres, Y.; Jenck, J. Adv. Organomet. Chem. 1991, 32, 121.