Productive utilization of chlorobenzene: Palladium-catalyzed selective oxidation of alcohols

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2485-2487

  Guram, Anil S ^a   Bei, Xiaohong ^a   Turner, Howard W ^a  

^a SYMYX TECHNOLOGIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; CHLOROBENZENE; FUNCTIONAL GROUP; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; TECHNIQUE;

EID: 0141519681     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0347287     Document Type: Article

References (35)

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10. Reviews: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. (b) Hartwig, J. F. Angew Chem., Int. Ed. 1998, 37, 2046-2067. (c) Beletskaya, I. P. Chem. Rev. 2000, 100, 3009-3066. (d) Grushin, V. V.; Alper, H. Top. Organomet. Chem. 1999, 3, 193-226. (e) Riermeier, T. H.; Zapf, A.; Beller, M. Top. Catal. 1997, 4, 301-309.
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15. Palladium-catalyzed oxidations based on chlorohydrocarbons: (a) Tamaru, Y.; Yamamoto, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 1401-1404. (b) Tamaru, Y.; Yamada, Y.; Inoue, K.; Yamamoto, Y.; Yoshida, Z. J. Org. Chem. 1983, 48, 1286-1292. (c) Nagashima, H.; Tsuji, J. Chem. Lett. 1981, 1171-1172. (d) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619-1620. (e) Poetsch, E.; Lannert, H. Chem. Abstr. 1996, 124, 145502d. (f) Bouquillon, S.; Henin, F.; Muzart, J. Organometallics 2000, 19, 1434-1437.
16. Palladium-catalyzed oxidations based on chlorohydrocarbons: (a) Tamaru, Y.; Yamamoto, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 1401-1404. (b) Tamaru, Y.; Yamada, Y.; Inoue, K.; Yamamoto, Y.; Yoshida, Z. J. Org. Chem. 1983, 48, 1286-1292. (c) Nagashima, H.; Tsuji, J. Chem. Lett. 1981, 1171-1172. (d) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619-1620. (e) Poetsch, E.; Lannert, H. Chem. Abstr. 1996, 124, 145502d. (f) Bouquillon, S.; Henin, F.; Muzart, J. Organometallics 2000, 19, 1434-1437.
17. Palladium-catalyzed oxidations based on chlorohydrocarbons: (a) Tamaru, Y.; Yamamoto, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 1401-1404. (b) Tamaru, Y.; Yamada, Y.; Inoue, K.; Yamamoto, Y.; Yoshida, Z. J. Org. Chem. 1983, 48, 1286-1292. (c) Nagashima, H.; Tsuji, J. Chem. Lett. 1981, 1171-1172. (d) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619-1620. (e) Poetsch, E.; Lannert, H. Chem. Abstr. 1996, 124, 145502d. (f) Bouquillon, S.; Henin, F.; Muzart, J. Organometallics 2000, 19, 1434-1437.
18. Palladium-catalyzed oxidations based on chlorohydrocarbons: (a) Tamaru, Y.; Yamamoto, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 1401-1404. (b) Tamaru, Y.; Yamada, Y.; Inoue, K.; Yamamoto, Y.; Yoshida, Z. J. Org. Chem. 1983, 48, 1286-1292. (c) Nagashima, H.; Tsuji, J. Chem. Lett. 1981, 1171-1172. (d) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619-1620. (e) Poetsch, E.; Lannert, H. Chem. Abstr. 1996, 124, 145502d. (f) Bouquillon, S.; Henin, F.; Muzart, J. Organometallics 2000, 19, 1434-1437.
19. Palladium-catalyzed oxidations based on chlorohydrocarbons: (a) Tamaru, Y.; Yamamoto, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 1401-1404. (b) Tamaru, Y.; Yamada, Y.; Inoue, K.; Yamamoto, Y.; Yoshida, Z. J. Org. Chem. 1983, 48, 1286-1292. (c) Nagashima, H.; Tsuji, J. Chem. Lett. 1981, 1171-1172. (d) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619-1620. (e) Poetsch, E.; Lannert, H. Chem. Abstr. 1996, 124, 145502d. (f) Bouquillon, S.; Henin, F.; Muzart, J. Organometallics 2000, 19, 1434-1437.
20. Palladium-catalyzed oxidations based on chlorohydrocarbons: (a) Tamaru, Y.; Yamamoto, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron Lett. 1979, 1401-1404. (b) Tamaru, Y.; Yamada, Y.; Inoue, K.; Yamamoto, Y.; Yoshida, Z. J. Org. Chem. 1983, 48, 1286-1292. (c) Nagashima, H.; Tsuji, J. Chem. Lett. 1981, 1171-1172. (d) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619-1620. (e) Poetsch, E.; Lannert, H. Chem. Abstr. 1996, 124, 145502d. (f) Bouquillon, S.; Henin, F.; Muzart, J. Organometallics 2000, 19, 1434-1437.
21. Leading references for palladium-catalyzed oxidations based on O-containing oxidants: (a) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157-158. (b) Petersen, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755. (d) Nagashima, H.; Tsuji J. Bull. Chem. Soc. Jpn. 1981, 1171-1172. (e) Tsuji, J.; Nagashima, H.; Sato, K. Tetrahedron Lett. 1982, 23, 3085-3088. (f) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620-6625.
22. Leading references for palladium-catalyzed oxidations based on O-containing oxidants: (a) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157-158. (b) Petersen, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755. (d) Nagashima, H.; Tsuji J. Bull. Chem. Soc. Jpn. 1981, 1171-1172. (e) Tsuji, J.; Nagashima, H.; Sato, K. Tetrahedron Lett. 1982, 23, 3085-3088. (f) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620-6625.
23. Leading references for palladium-catalyzed oxidations based on O-containing oxidants: (a) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157-158. (b) Petersen, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755. (d) Nagashima, H.; Tsuji J. Bull. Chem. Soc. Jpn. 1981, 1171-1172. (e) Tsuji, J.; Nagashima, H.; Sato, K. Tetrahedron Lett. 1982, 23, 3085-3088. (f) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620-6625.
24. Leading references for palladium-catalyzed oxidations based on O-containing oxidants: (a) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157-158. (b) Petersen, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755. (d) Nagashima, H.; Tsuji J. Bull. Chem. Soc. Jpn. 1981, 1171-1172. (e) Tsuji, J.; Nagashima, H.; Sato, K. Tetrahedron Lett. 1982, 23, 3085-3088. (f) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620-6625.
25. Leading references for palladium-catalyzed oxidations based on O-containing oxidants: (a) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157-158. (b) Petersen, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755. (d) Nagashima, H.; Tsuji J. Bull. Chem. Soc. Jpn. 1981, 1171-1172. (e) Tsuji, J.; Nagashima, H.; Sato, K. Tetrahedron Lett. 1982, 23, 3085-3088. (f) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620-6625.
26. Leading references for palladium-catalyzed oxidations based on O-containing oxidants: (a) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157-158. (b) Petersen, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755. (d) Nagashima, H.; Tsuji J. Bull. Chem. Soc. Jpn. 1981, 1171-1172. (e) Tsuji, J.; Nagashima, H.; Sato, K. Tetrahedron Lett. 1982, 23, 3085-3088. (f) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620-6625.
27. Details of high-throughput methods and additional experimental results will be reported separately in a full article.
28. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
29. 4, filtered, and concentrated under vacuum. The crude product was purified by column chromatography on silica gel to afford 4,4′-diflourobenzophenone as an off-white solid (215 mg, 98%) after drying under vacuum.
30. These intermediates are of significance as perfume additives in the fragrance industry; see: (a) Naarden & Shell Aroma Chemicals. German Patent Application DE 2,945,812, 1980. (b) Kao Corp. Japanese Patent Application JP 92-77446, 1992.
31. These intermediates are of significance as perfume additives in the fragrance industry; see: (a) Naarden & Shell Aroma Chemicals. German Patent Application DE 2,945,812, 1980. (b) Kao Corp. Japanese Patent Application JP 92-77446, 1992.
32. The Pd/L-catalyzed oxidation of sterically less hindered aliphatic alcohols was not rigorously investigated or optimized. Aldol reaction induced inefficiencies were observed in preliminary studies. However, it is anticipated that such inefficiencies could be alleviated under optimized reaction conditions
33. Steric factors are known to favor the reductive elimination process; see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395-3396. (b) Jones, W. D.; Kuykendall, V. L. Inorg. Chem. 1991, 30, 2615-2622. For pioneering studies of C-O bond forming reductive elimination from nickel complexes, see: (c) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135-8136.
34. Steric factors are known to favor the reductive elimination process; see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395-3396. (b) Jones, W. D.; Kuykendall, V. L. Inorg. Chem. 1991, 30, 2615-2622. For pioneering studies of C-O bond forming reductive elimination from nickel complexes, see: (c) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135-8136.
35. Steric factors are known to favor the reductive elimination process; see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395-3396. (b) Jones, W. D.; Kuykendall, V. L. Inorg. Chem. 1991, 30, 2615-2622. For pioneering studies of C-O bond forming reductive elimination from nickel complexes, see: (c) Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135-8136.