Heck-type cyclization of oxime ethers: Stereoselective carbon-carbon bond formation with aryl halides to produce heterocyclic oximes

Angewandte Chemie - International Edition

Volumn 46, Issue 33, 2007, Pages 6325-6328

  Ohno, Hiroaki ^a   Aso, Akimasa ^b   Kadoh, Yoichi ^b   Fujii, Nobutaka ^a   Tanaka, Tetsuaki ^b  

^a KYOTO UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Cyclization; Heck reaction; Heterocycles; Oxime ethers; Palladium

Indexed keywords

CYCLIZATION; HALOGEN COMPOUNDS; PALLADIUM; STEREOSELECTIVITY; TOLUENE;

CARBON-CARBON BONDS; HECK REACTION; HETEROCYCLES; OXIME ETHERS;

ETHERS;

ETHER DERIVATIVE; HALOGEN; HETEROCYCLIC COMPOUND; OXIME;

ARTICLE; CHEMISTRY; CYCLIZATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; ULTRAVIOLET SPECTROPHOTOMETRY;

CYCLIZATION; ETHERS; HALOGENS; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; OXIMES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 34548280259     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701868     Document Type: Article

References (48)

1. a) H. Nakamura, H. Iwama, Y. Yamamoto, J. Am. Chem. Soc. 1996, 118, 6641-6647;
2. b) H. Nakamura, K. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 4242-4243;
3. c) K. Nakamura, H. Nakamura, Y. Yamamoto, J. Org. Chem. 1999, 64, 2614-2615;
4. d) S. Sebelius, O. A. Wallner, K. J. Szabó, Org. Lett. 2003, 5, 3065-3068.
5. For a related reaction of (aryl)allylpalladium complexes, see: a) N. Solin, J. Kjellgren, K. J. Szabó, J. Am. Chem. Soc. 2004, 126, 7026-7033;
6. b) C. D Hopkins, H. C. Malinakova, Org. Lett. 2006, 8, 5971-5974.
7. For related allylindium-mediated reactions, see: a) H. Miyabe, Y. Yamaoka, T. Naito, Y. Takemoto, J. Org. Chem. 2003, 68, 6745-6751;
8. b) H. Miyabe, Y. Yamaoka, T. Naito, Y. Takemoto, J. Org. Chem. 2004, 69, 1415-1418.
9. a) R. C. Larock, Q. Tian, A. A. Pletnev, J. Am. Chem. Soc. 1999, 121, 3238-3239;
10. b) C. Zhou, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 2302-2303.
11. For the insertion of imines into complexes of other metals, see: a) G. Vasapollo, H. Alper, Tetrahedron Lett. 1988, 29, 5113-5116;
12. b) F. Muller, G. van Koten, K. Vrieze, Organometallics 1989, 8, 33-40;
13. c) M. D. Fryzuk, W. E. Piers, Organometallics 1990, 9, 986-998;
14. d) A. C. Reduto dos Reis, L. S. Hegedus, Organometallics 1995, 14, 1586-1591.
15. The insertion of an imine into a palladium-acyl bond is a more facile process than the insertion of an imine into other carbon-palladium bonds as a result of the additional driving force derived from the formation of a strong amide linkage; see: L. Cavallo, J. Am. Chem. Soc. 1999, 121, 4238-4241.
16. R. D. Dghaym, K. J. Yaccato, B. A. Arndtsen, Organometallics 1998, 17, 4-6.
17. S. Kacker, J. S. Kim, A. Sen, Angew. Chem. 1998, 110, 1335-1337;
18. Angew. Chem. Int. Ed. 1998, 37, 1251-1253.
19. A. Takeda, S. Kamijo, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 5662-5663.
20. For a related reaction, see: K. R. Roesch, R. C. Larock, Org. Lett. 1999, 1, 1551-1553.
21. a) H. Ohno, K. Miyamura, Y. Takeoka, T. Tanaka, Angew. Chem. 2003, 115, 2751-2754;
22. Angew. Chem. Int. Ed. 2003, 42, 2647-2650;
23. b) H. Ohno, Y. Takeoka, K. Miyamura, Y. Kadoh, T. Tanaka, Org. Lett. 2003, 5, 4763-4766;
24. c) H. Ohno, Y. Takeoka, Y. Kadoh, K. Miyamura, T. Tanaka, J. Org. Chem. 2004, 69, 4541-4544;
25. d) H. Ohno, T. Mizutani, Y. Kadoh, K. Miyamura, T. Tanaka, Angew. Chem. 2005, 117, 5243-5245;
26. Angew. Chem. Int. Ed. 2005, 44, 5113-5115;
27. e) H. Ohno, K. Miyamura, T. Mizutani, Y. Kadoh, Y. Takeoka, H. Hamaguchi, T. Tanaka, Chem. Eur. J. 2005, 11, 3728-3741;
28. f) H. Ohno, T. Mizutani, Y. Kadoh, A. Aso, K.. Miyamura, N. Fujii, T. Tanaka, J. Org. Chem. 2007, 72, 4378-4389.
29. For recent reviews, see: a) H. Ohno, Yakugaku Zasshi 2001, 121, 733-741;
30. b) H. Ohno, Chem. Pharm. Bull. 2005, 53, 1211-1226;
31. c) H. Ohno, Yakugaku Zasshi 2005, 125, 899-925.
32. R. Grigg, J. Markandu, Tetrahedron Lett. 1991, 32, 279-282.
33. a) G. Mann, J. F. Hartwig, M. S. Driver, C. Fernández-Rivas, J. Am. Chem. Soc. 1998, 120, 827-828;
34. b) H. Tsutsui, M. Kitamura, K. Narasaka, Bull. Chem. Soc. Jpn. 2002, 75, 1451-1460;
35. c) S. Chiba, M. Kitamura, O. Saku, K. Narasaka, Bull. Chem. Soc. Jpn. 2004, 77, 785-796.
36. T. Nishimura, Y. Nishiguchi, Y. Maeda, S. Uemura, J. Org. Chem. 2004, 69, 5342-5347.
37. a) L. V. Desai, K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2004, 126, 9542-9543;
38. b) H.-Y. Thu, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2006, 128, 9048-9049.
39. For a recent review on radical carbon-carbon bond formation with oxime ethers, see: H. Miyabe, M. Ueda, T. Naito, Synlett 2004, 1140-1157.
40. a) O. Miyata, M. Namba, M. Ueda, T. Naito, Chem. Commun. 2004, 1274-1276;
41. b) H. Miyabe, M. Ueda, K. Fujii, A. Nishimura, T. Naito, J. Org. Chem. 2003, 68, 5618-5626.
42. 13C NMR spectra with those of related compounds; see: a) D. R. Williams, M. H. Osterhout, J. Am. Chem. Soc. 1992, 114, 8750-8751;
43. b) M. S. Gordon, S. A. Sojka, J. Org. Chem. 1984, 49, 97-100.
44. -1; for details, see: H. Kessler, D. Leibfritz, Tetrahedron Lett. 1970, 11, 4293-4296.
45. For an excellent review, see: A. Rauk, L. C. Allen, K. Mislow, Angew. Chem. 1970, 82, 453-468;
46. Angew. Chem. Int. Ed. Engl. 1970, 9, 400-414.
47. For a recent ab initio study, see: M. Tanaka, M. Aida, Chem. Phys. Lett. 2006, 417, 316-319.
48. [9] However, our proposed mechanism (Scheme 4), in which an aryl palladium species undergoes unprecedented insertion into an oxime ether (e.g. 15→16), better explains the observed stereochemical outcome. For a related mechanism, see: J. Zhao, D. Yue, M. A. Campo, R. C. Larock, J. Am. Chem. Soc. 2007, 129, 5288-5295.