Nickel(o)-mediated [3+2+2] and [2+2+2+1] cyclization reactions of chromium Fischer carbene complexes and alkynes

Angewandte Chemie - International Edition

Volumn 42, Issue 26, 2003, Pages 3008-3011

  Barluenga, José ^a   Barrio, Pablo ^a   López, Luis A ^a   Tomás, Miguel ^a   García Granda, Santiago ^a   Alvarez Rúa, Carmen ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Alkynes; Carbene ligands; Chromium; Cyclization; Nickel

Indexed keywords

COMPLEXATION; NICKEL; PHENOLS;

REGIOSELECTIVITY;

REACTION KINETICS;

ALKYNE; CARBENE; CHROMIUM; NICKEL; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY;

EID: 0041305921     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351216     Document Type: Article

References (42)

1. W. D. Wulff in Comprehensive Organometallic Chemistry II, VoL 12 (Eds.: E. W. Abel, F. G. A., Stone, G. Wilkinson), Pergamon, New York, 1995, p. 469.
2. B. Gabor, C. Krüger, B. Marczinke, R. Mynott, G. Wilke, Angew. Chem. 1991, 103, 1711; Angew. Chem. Int. Ed. Engl. 1991, 30, 1666.
3. B. Gabor, C. Krüger, B. Marczinke, R. Mynott, G. Wilke, Angew. Chem. 1991, 103, 1711; Angew. Chem. Int. Ed. Engl. 1991, 30, 1666.
4. a) L. Simunic, A. R. Pinhas, Organometallics 1987, 6, 1358;
5. b) L. Simunic, A. R. Pinhas, Inorg. Chem. 1989, 28, 2400.
6. II aminocarbene complex, see A. C. Albéniz, P. Espinet, R. Manrique, A. Pérez-Mateo, Angew. Chem. 2002, 114, 2469; Angew. Chem. Int. Ed. 2002, 41, 2363.
7. II aminocarbene complex, see A. C. Albéniz, P. Espinet, R. Manrique, A. Pérez-Mateo, Angew. Chem. 2002, 114, 2469; Angew. Chem. Int. Ed. 2002, 41, 2363.
8. J. Barluenga, L. A. López, O. Löber, M. Tomás, S. García-Granda, C. Alvarez-Rúa, J. Borge, Angew. Chem. 2001, 113, 3495; Angew. Chem. Int. Ed. 2001, 40, 3392.
9. J. Barluenga, L. A. López, O. Löber, M. Tomás, S. García-Granda, C. Alvarez-Rúa, J. Borge, Angew. Chem. 2001, 113, 3495; Angew. Chem. Int. Ed. 2001, 40, 3392.
10. a) T. Liu, K. R. Reddy, Chem. Soc. Rev. 1999, 28, 315;
11. b) R.-Z. Ku, J.-C. Huang, J.-Y. Cho, F.-M. Kiang, K. R. Reddy, Y.-C. Chen, K.-J. Lee, J.-H. Lee, G.-H. Lee, S.-M. Peng, S.-T. Liu, Organometallics 1999, 18, 2145.
12. 5], see E. O. Fischer, H.-J. Beck, C. G. Kreiter, J. Lynch, J. Müller, E. Winkler, Chem. Ber. 1972, 105, 162;
13. 4], see R. Aumann, E. O. Fischer, Chem. Ber. 1981, 114, 1853;
14. 2], see ref. [4].
15. In several papers Sierra et al. have proposed palladium biscarbene complexes as the active intermediates in the palladium-catalyzed dimerization of chromium alkoxycarbene complexes: a) M. A. Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812; b) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, J. Am. Chem. Soc. 2001, 123, 851; c) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, M. R. Torres, Chem. Commun. 2002, 1842. Other carbene species of Rh, Cu, and Pd have been proposed as intermediates: d) I. Göttker-Schnetmann, R. Aumann, Organometallics 2001, 20, 346; e) I. Göttker-Schnetmann, R. Aumann, K. Bergander, Organometallics 2001, 20, 3574; f) R. Aumann, I. Göttker-Schnetmann, R. Fröhlich, O. Meyer, Eur. J. Org. Chem. 1999, 2545; g) H. Sakurai, K. Tanabe, K. Narasaka, Chem. Lett. 1999, 75.
16. In several papers Sierra et al. have proposed palladium biscarbene complexes as the active intermediates in the palladium-catalyzed dimerization of chromium alkoxycarbene complexes: a) M. A. Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812; b) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, J. Am. Chem. Soc. 2001, 123, 851; c) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, M. R. Torres, Chem. Commun. 2002, 1842. Other carbene species of Rh, Cu, and Pd have been proposed as intermediates: d) I. Göttker-Schnetmann, R. Aumann, Organometallics 2001, 20, 346; e) I. Göttker-Schnetmann, R. Aumann, K. Bergander, Organometallics 2001, 20, 3574; f) R. Aumann, I. Göttker-Schnetmann, R. Fröhlich, O. Meyer, Eur. J. Org. Chem. 1999, 2545; g) H. Sakurai, K. Tanabe, K. Narasaka, Chem. Lett. 1999, 75.
17. In several papers Sierra et al. have proposed palladium biscarbene complexes as the active intermediates in the palladium-catalyzed dimerization of chromium alkoxycarbene complexes: a) M. A. Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812; b) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, J. Am. Chem. Soc. 2001, 123, 851; c) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, M. R. Torres, Chem. Commun. 2002, 1842. Other carbene species of Rh, Cu, and Pd have been proposed as intermediates: d) I. Göttker-Schnetmann, R. Aumann, Organometallics 2001, 20, 346; e) I. Göttker-Schnetmann, R. Aumann, K. Bergander, Organometallics 2001, 20, 3574; f) R. Aumann, I. Göttker-Schnetmann, R. Fröhlich, O. Meyer, Eur. J. Org. Chem. 1999, 2545; g) H. Sakurai, K. Tanabe, K. Narasaka, Chem. Lett. 1999, 75.
18. In several papers Sierra et al. have proposed palladium biscarbene complexes as the active intermediates in the palladium-catalyzed dimerization of chromium alkoxycarbene complexes: a) M. A. Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812; b) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, J. Am. Chem. Soc. 2001, 123, 851; c) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, M. R. Torres, Chem. Commun. 2002, 1842. Other carbene species of Rh, Cu, and Pd have been proposed as intermediates: d) I. Göttker-Schnetmann, R. Aumann, Organometallics 2001, 20, 346; e) I. Göttker-Schnetmann, R. Aumann, K. Bergander, Organometallics 2001, 20, 3574; f) R. Aumann, I. Göttker-Schnetmann, R. Fröhlich, O. Meyer, Eur. J. Org. Chem. 1999, 2545; g) H. Sakurai, K. Tanabe, K. Narasaka, Chem. Lett. 1999, 75.
19. In several papers Sierra et al. have proposed palladium biscarbene complexes as the active intermediates in the palladium-catalyzed dimerization of chromium alkoxycarbene complexes: a) M. A. Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812; b) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, J. Am. Chem. Soc. 2001, 123, 851; c) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, M. R. Torres, Chem. Commun. 2002, 1842. Other carbene species of Rh, Cu, and Pd have been proposed as intermediates: d) I. Göttker-Schnetmann, R. Aumann, Organometallics 2001, 20, 346; e) I. Göttker-Schnetmann, R. Aumann, K. Bergander, Organometallics 2001, 20, 3574; f) R. Aumann, I. Göttker-Schnetmann, R. Fröhlich, O. Meyer, Eur. J. Org. Chem. 1999, 2545; g) H. Sakurai, K. Tanabe, K. Narasaka, Chem. Lett. 1999, 75.
20. In several papers Sierra et al. have proposed palladium biscarbene complexes as the active intermediates in the palladium-catalyzed dimerization of chromium alkoxycarbene complexes: a) M. A. Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812; b) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, J. Am. Chem. Soc. 2001, 123, 851; c) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, M. R. Torres, Chem. Commun. 2002, 1842. Other carbene species of Rh, Cu, and Pd have been proposed as intermediates: d) I. Göttker-Schnetmann, R. Aumann, Organometallics 2001, 20, 346; e) I. Göttker-Schnetmann, R. Aumann, K. Bergander, Organometallics 2001, 20, 3574; f) R. Aumann, I. Göttker-Schnetmann, R. Fröhlich, O. Meyer, Eur. J. Org. Chem. 1999, 2545; g) H. Sakurai, K. Tanabe, K. Narasaka, Chem. Lett. 1999, 75.
21. In several papers Sierra et al. have proposed palladium biscarbene complexes as the active intermediates in the palladium-catalyzed dimerization of chromium alkoxycarbene complexes: a) M. A. Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812; b) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, J. Am. Chem. Soc. 2001, 123, 851; c) M. A. Sierra, J. C. del Amo, M. J. Mancheño, M. Gómez-Gallego, M. R. Torres, Chem. Commun. 2002, 1842. Other carbene species of Rh, Cu, and Pd have been proposed as intermediates: d) I. Göttker-Schnetmann, R. Aumann, Organometallics 2001, 20, 346; e) I. Göttker-Schnetmann, R. Aumann, K. Bergander, Organometallics 2001, 20, 3574; f) R. Aumann, I. Göttker-Schnetmann, R. Fröhlich, O. Meyer, Eur. J. Org. Chem. 1999, 2545; g) H. Sakurai, K. Tanabe, K. Narasaka, Chem. Lett. 1999, 75.
22. a) C. P. Kubiak in Comprehensive Organometallic Chemistry II, Vol. 9 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, New York, 1995, p. 1.
23. Selected references: b) V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, Angew. Chem. 2001, 113, 3500; Angew. Chem. Int. Ed. 2001, 40, 3387;
24. Selected references: b) V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, Angew. Chem. 2001, 113, 3500; Angew. Chem. Int. Ed. 2001, 40, 3387;
25. c) Y. Sato, M. Takimoto, M. Mori, J. Am. Chem. Soc. 2000, 122, 1624.
26. 3] dimerize rapidly at room temperature and at low temperature, respectively. See ref. [3b].
27. o was first reported by Arduengo et al.: A. J. Arduengo III, S. F. Gamper, J. C. Calabrese, F. Davidson, J. Am. Chem. Soc. 1994, 116, 4391;
28. o, see D. J. Mindiola, G. L. Hillhouse, J. Am. Chem. Soc. 2002, 124, 9976.
29. K. H. Dötz, Angew. Chem. 1984, 96, 573; Angew. Chem. Int. Ed. Engl. 1984, 23, 587.
30. K. H. Dötz, Angew. Chem. 1984, 96, 573; Angew. Chem. Int. Ed. Engl. 1984, 23, 587.
31. It was found for related complexes that the coupling constant between H6 and H7 is about 8 Hz for the exo isomer and about 2 Hz for the endo isomer: S. D. Reynolds, T. A. Albright, Organometallics 1985, 4, 980.
32. See Supporting Information for crystal data of 5b and 8e.
33. 2] is used the yield of 5 a drops to 45 % and about half of the carbene complex la is recovered.
34. a) The insertion of alkynes into nickel carbene complexes was demonstrated by Eisch et al. in the cross-oligomerization of alkynes with carbene sources to give substituted cyclopentadienes: J. J. Eisch, A. A. Aradi, M. A. Lucarelli, Y. Qian, Tetrahedron 1998, 54, 1169;
35. b) The insertion of carbonyl and sulfur substrates into a diphenylcarbene nickel complex has been just reported (ref. [11b]).
36. a) For a related formation of oxepines by alkyne insertion into a rhodium carbene complex, see A. Padwa, S. L. Xu, J. Am. Chem. Soc. 1992, 114, 5881;
37. b) For the norcaradiene-cycloheptatriene equilibrium, see A. A. Jarzecki, J. Gajewski, E. R. Davidson, J. Am. Chem. Soc. 1999, 121, 6928.
38. R. H. Rigby, Tetrahedron 1999, 55, 4521.
39. a) For an elegant allyl/alkyne [3+2+2] cycloaddition mediated by cobalt, see N. Etkin, T. L. Dzwiniel, K. E. Schweibert, J. M. Stryker, J. Am. Chem. Soc. 1998, 120, 9702;
40. b) For the carbonylative cyclization of enediynes, see I. Ojima, S.-Y. Lee, J. Am. Chem. Soc. 2000, 122, 2385.
41. The [2+2+1+1] cyclization of simple Fischer carbene complexes and alkynes has been reported: W. D. Wulf, R. W. Kaesler, G. A. Peterson, P.-C. Tang, J. Am. Chem. Soc. 1985, 107, 1060.
42. 2], albeit in somewhat lower yield than with 1.1 equivalents (55 versus 75 %).