Heteropolyacid-catalyzed direct deoxygenation of propargyl and allyl alcohols

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 7092-7097

  Egi, Masahiro ^a   Kawai, Takuya ^a   Umemura, Megumi ^a   Akai, Shuji ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOLS; DEOXYGENATIONS; DOUBLE BONDS; PRODUCT YIELDS; PROPARGYL; PROPARGYL ALCOHOL; SOLVENT SELECTION; THERMODYNAMICALLY STABLE;

CHEMISTRY; ORGANIC COMPOUNDS;

OLEFINS;

1 (2 PHENYLETHYNYL)CYCLOHEXANOL; 1 (3 CCHLOROPHENYL) 2 NONYNE; 1 (3 CHLOROPHENYL) 2 NONYN 1 OL; 1 (3 PHENYL 2 PROPYNYL)NAPHTHALENE; 1 (4 CHLOROPHENYL) 2 NONYNE; 1 (4 CHLOROPHENYL) 3 PHENYL 2 PROPYN 1 OL; 1 (4 METHOXYPHENYL) 2 NONYN 1 OL; 1 (4 METHOXYPHENYL) 2 NONYNE; 1 (4 METHYLPHENYL) 2 NONYNE; 1 NAPHTHALEN 1 YL 3 PHENYL 2 PROPYN 1 OL; 1 PHENYL 2 NONYNE; 1 PHENYL 3 TRIISOPROPYLSILYL 2 PROPYN 1 OL; 1 PHENYLCYCLOHEXENE; 1,1 DICYCLOHEXYL 5 PHENYL 1 PENTENE; 1,1 DICYCLOHEXYL 5 PHENYL 2 PENTEN 1 OL; 1,1 DIPHENYL 1 BUTENE; 1,1 DIPHENYL 2 BUTEN 1 OL; 1,1 DIPHENYL 2 BUTYN 1 OL; 1,3 DIPHENYL 1 PROPYNE; 2 BENZYL 1 PHENYL 2 PENTENE; 2 BENZYL 1 PHENYL 3 PENTEN 2 OL; 3 (4 CHLOROPHENYL) 1 PHENYL 1 PROPYNE; 3 PHENETHYL 1 PHENYL 3 HEPTENE; 3 PHENETHYL 1 PHENYL 4 HEPTEN 3 OL; 4,4 DIMETHYL 1 PHENYL 2 PENTYNE; ALCOHOL; ALKENE; ALLYL ALCOHOL; PROPARGYL ALCOHOL; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; DEOXYGENATION; THERMODYNAMICS;

ALKENES; ALKYNES; CATALYSIS; OXYGEN; PHOSPHOTUNGSTIC ACID; PROPANOLS; SOLVENTS; THERMODYNAMICS;

EID: 84865205426     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300889p     Document Type: Article

References (47)

1. Okuhara, T.; Mizuno, N.; Misono, M. Adv. Catal. 1996, 41, 113-252
2. Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171-198
3. Hill, C. L. J. Mol. Catal. A: Chem. 2007, 262, 1-242
4. Long, D.-L.; Tsunashima, R.; Cronin, L. Angew. Chem., Int. Ed. 2010, 49, 1736-1758
5. Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M. J. Org. Chem. 1988, 53, 3587-3593
6. Ben-Daniel, R.; Alsters, P.; Neumann, R. J. Org. Chem. 2001, 66, 8650-8653
7. Aakel, L. E.; Launay, F.; Atlamsani, A.; Brégeault, J.-M. Chem. Commun. 2001, 2218-2219
8. Bordoloi, A.; Lefebvre, F.; Halligudi, S. B. J. Catal. 2007, 247, 166-175
9. Mizuno, N.; Kamata, K.; Yamaguchi, K. Top. Catal. 2010, 53, 876-893
10. Kogan, V.; Aizenshtat, Z.; Neumann, R. Angew. Chem., Int. Ed. 1999, 38, 3331-3334
11. Heydari, A.; Khaksar, S.; Akbari, J.; Esfandyari, M.; Pourayoubi, M.; Tajbakhsh, M. Tetrahedron Lett. 2007, 48, 1135-1138
12. Akai, S.; Tanimoto, K.; Kanao, Y.; Egi, M.; Yamamoto, T.; Kita, Y. Angew. Chem., Int. Ed. 2006, 45, 2592-2595
13. Egi, M.; Yamaguchi, Y.; Fujiwara, N.; Akai, S. Org. Lett. 2008, 10, 1867-1870
14. Akai, S.; Hanada, R.; Fujiwara, N.; Kita, Y.; Egi, M. Org. Lett. 2010, 12, 4900-4903
15. Egi, M.; Umemura, M.; Kawai, T.; Akai, S. Angew. Chem., Int. Ed. 2011, 50, 12197-12200
16. Drago, R. S.; Dias, J. A.; Maier, T. O. J. Am. Chem. Soc. 1997, 119, 7702-7710
17. Shuklov, I. A.; Dubrovina, N. V.; Börner, A. Synthesis 2007, 2925-2943
18. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207-214
19. Teobald, B. J. Tetrahedron 2002, 58, 4133-4170
20. Clarke, P. A.; Cridland, A. P.; Rolla, G. A.; Iqbal, M.; Bainbridge, N. P.; Whitwood, A. C.; Wilson, C. J. Org. Chem. 2009, 74, 7812-7821
21. Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2005, 127, 4763-4776
22. Saito, T.; Furukawa, N.; Otani, T. Org. Biomol. Chem. 2010, 8, 1126-1132
23. Madu, C. E.; Seshadri, H.; Lovely, C. J. Tetrahedron 2007, 63, 5019-5029
24. Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2005, 46, 6407-6409
25. Nishibayashi, Y.; Shinoda, A.; Miyake, Y.; Matsuzawa, H.; Sato, M. Angew. Chem., Int. Ed. 2006, 45, 4835-4839
26. Yuki, M.; Miyake, Y.; Nishibayashi, Y. Organometallics 2010, 29, 5994-6001
27. Georgy, M.; Boucard, V.; Debleds, O.; Dal Zotto, C.; Campagne, J.-M. Tetrahedron 2009, 65, 1758-1766
28. Debleds, O.; Gayon, E.; Vrancken, E.; Campagne, J.-M. Beilstein J. Org. Chem. 2011, 7, 866-877
29. 2-catalyzed deoxygenation of propargyl alcohols. See: Meyer, V. J.; Niggemann, M. Chem.-Eur. J. 2012, 18, 4687-4691
30. Yasuda, M.; Onishi, Y.; Ueba, M.; Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741-7744
31. Wang, J.; Huang, W.; Zhang, Z.; Xiang, X.; Liu, R.; Zhou, X. J. Org. Chem. 2009, 74, 3299-3304
32. Chan, L. Y.; Lim, J. S. K.; Kim, S. Synlett 2011, 2862-2866
33. Fan, J.; Wan, C.; Wang, Q.; Gao, L.; Zheng, X.; Wang, Z. Org. Biomol. Chem. 2009, 7, 3168-3172
34. Zhu, H.-T.; Ji, K.-G.; Yang, F.; Wang, L.-J.; Zhao, S.-C.; Ali, S.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2011, 13, 684-687
35. Downey, C. W.; Mahoney, B. D.; Lipari, V. R. J. Org. Chem. 2009, 74, 2904-2906
36. Lee, T.; Kang, H. R.; Kim, S.; Kim, S. Tetrahedron 2006, 62, 4081-4085
37. Csékei, M.; Novák, Z.; Kotschy, A. Tetrahedron 2008, 64, 975-982
38. Kong, W.; Guo, B.; Fu, C.; Ma, S. Eur. J. Org. Chem. 2011, 2278-2285
39. Zhang, W.-W.; Zhang, X.-G.; Li, J.-H. J. Org. Chem. 2010, 75, 5259-5264
40. Torregrosa, R. R. P.; Ariyarathna, Y.; Chattopadhyay, K.; Tunge, J. A. J. Am. Chem. Soc. 2010, 132, 9280-9282
41. Tsutsumi, K.; Ogoshi, S.; Kakiuchi, K.; Nishiguchi, S.; Kurosawa, H. Inorg. Chim. Acta 1999, 296, 37-44
42. Ma, S.; He, Q. Tetrahedron 2006, 62, 2769-2778
43. Fleming, I.; Ramarao, C. Org. Biomol. Chem. 2004, 2, 1504-1510
44. Lee, C.-L.; Huang, C.-H.; Wang, H.-C.; Chuang, D.-W.; Wu, M.-J.; Wang, S.-Y.; Hwang, T.-L.; Wu, C.-C.; Chen, Y.-L.; Chang, F.-R.; Wu, Y.-C. Org. Biomol. Chem. 2011, 9, 70-73
45. Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138-2152
46. Zhao, X.; Jing, J.; Lu, K.; Zhang, Y.; Wang, J. Chem. Commun. 2010, 46, 1724-1726
47. Yanagisawa, A.; Nezu, T.; Mohri, S. Org. Lett. 2009, 11, 5286-5289