Rhodium-catalyzed decarbonylative coupling reactions of diphenylketene with alkenes

ChemCatChem

Volumn 1, Issue 1, 2009, Pages 82-84

  Kondo, Teruyuki ^a   Tokoro, Yukiko ^a   Ura, Yasuyuki ^b   Wada, Kenji ^a   Mitsudo, Take Aki ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NARA WOMEN'S UNIVERSITY   (Japan)

Author keywords

C C coupling; Carbenes; Homogeneous catalysis; Ketenes; Rhodium

Indexed keywords

C-C COUPLING; CARBENES; COUPLING REACTION; ELECTRON-DEFICIENT; HOMOGENEOUS CATALYSIS; KETENES; RHODIUM-CATALYZED; TERMINAL ALKENES;

HYDROCARBONS; REACTION KINETICS; RHODIUM;

CATALYSIS;

EID: 77954275309     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.200900075     Document Type: Article

References (44)

1. For reviews, see: In a) The Chemistry of Functional Groups: The Chemistry of Ketenes, Allenes, and Related Compounds Part 1 and Part 2 (Ed: S. Patai), Wiley, New York, 1980;
2. b) T. T. Tidwell, Sci. Synth. 2006, 23, 15-51
3. b) T. T. Tidwell, Sci. Synth. 2006, 23, 391-492
4. b) T. T. Tidwell, Sci. Synth. 2006, 23, 569-678;
5. c) A. Rafai Far, Angew. Chem. 2003, 115, 2442-2450
6. c) Angew. Chem. Int. Ed. 2003, 42, 2340-2348.
7. For example, see: a) E. O. Fischer, A. C. Filippou, H. G. Alt, K. Ackermann, J. Organomet. Chem. 1983, 254, C21-C23;
8. b) M. Wiederhold, U. Behrens, J. Organomet. Chem. 1994, 476, 101-109. For reviews, see
9. c) G. L. Geoffroy, S. L. Bassner, Adv. Organomet. Chem. 1988, 28, 1-83;
10. d) S. E. Gibson, M. A. Peplow, Adv. Organomet. Chem. 1999, 44, 275-355.
11. H. Okumoto in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed: E. Negishi), Wiley, New York, 2002, pp. 2655-2662.
12. In Comprehensive Organometallic Chemistry II, Vol. 12 (Eds: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, Chap. 5, pp. 469-547.
13. K. H. Dçtz, Angew. Chem. 1984, 96, 573-594
14. Angew. Chem. Int. Ed. Engl. 1984, 23, 587-608.
15. L. S. Hegedus, Tetrahedron 1997, 53, 4105-4128.
16. A. B. Bueno, W. H. Moser, L. S. Hegedus, J. Org. Chem. 1998, 63, 1462-1466.
17. a) D. B. Grotjahn, G. A. Bikzhanova, L. S. B. Collins, T. Concolino, K.-C. Lam, A. L. Rheingold, J. Am. Chem. Soc. 2000, 122, 5222-5223.
18. b) P. Hong, N. Nishi, K. Sonogashira, N. Hagihara, J. Chem. Soc. Chem. Commun. 1972, 993;
19. c) T. Yamamoto, A. R. Garber, J. R. Wilkinson, C. B. Boss, W. E. Streib, L. J. Todd, J. Chem. Soc. Chem. Commun. 1974, 354-356;
20. d) A. J. Arce, A. J. Deeming, J. Chem. Soc. Chem. Commun. 1982, 364-365;
21. e) E. D. Morrison, G. R. Steinmetz, G. L. Geoffroy, W. C. Fultz, A. L. Rheingold, J. Am. Chem. Soc. 1984, 106, 4783-4789.
22. a) A. Miyashita, H. Shitara, H. Nohira, Organometallics 1985, 4, 1463-1464;
23. b) A. Miyashita, R. Sugai, J. Yamamoto, J. Organomet. Chem. 1992, 428, 239-247;
24. c) C. A. Wright, M. Thorn, J. W. McGill, A. Sutterer, S. M. Hinze, R. B. Prince, J. K. Gong, J. Am. Chem. Soc. 1996, 118, 10305-10306.
25. T. Kondo, M. Nomura, Y. Ura, K. Wada, T. Mitsudo, Tetrahedron Lett. 2006, 47, 7107-7111.
26. T. Kondo, M. Nomura, Y. Ura, K. Wada, T. Mitsudo, J. Am. Chem. Soc. 2006, 128, 14816-14817.
27. a) T. Mitsudo, M. Kadokura, Y. Watanabe, Tetrahedron Lett. 1985, 26, 3697-3698. For related condensation reactions using ketenes, see
28. b) T. Mitsudo, M. Kadokura, Y. Watanabe, J. Org. Chem. 1987, 52, 1695-1699;
29. c) T. Mitsudo, M. Kadokura, Y. Watanabe, J. Org. Chem. 1987, 52, 3186-3192.
30. Palladium-catalyzed C Coupling reactions of 2-norbornenes with diphenylketene were recently reported. However, the applicable alkenes were strictly limited to strained 2-norbornenes. J. M. Goll, E. Fillion, Organometallics 2008, 27, 3622-3625.
31. Crystal data for 3a: C20H20 ; Mr=260.38; crystal size 0.50×0.20× 0.10 mm; monoclinic; space group P21/a; a=11.823(3), b=14.199(2), c=9.049(2) Å; β=101.56(2)°; V=1488.2(6) Å3 ; Z=4; ρcalcd= 1.162 gcm-3 ; μ(MoKα)=0.7107 Å; 3411 reflections measured, 1505 unique reflections were collected on a Rigaku AFC 7R diffractometer at 298.2 K (2θ<55.0°); Rint=0.0454; wR2=0.1415; GOF=1.024. CCDC 726164 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif.
32. a) J. W. Wilt, M. Peeran, S. Ramakrishnan, D. S. Crumrine, Magn. Reson. Chem. 1989, 27, 323-327;
33. b) M. Peeran, J. W. Wilt, R. Subramanian, D. S. Crumrine, J. Org. Chem. 1993, 58, 202-210.
34. Transition metal complex-catalyzed or-mediated reactions of styrene with diphenyldiazomethane or ethyl diazoacetate are known to give the corresponding cyclopropanes: a) Y. Lie, J.-S. Huang, Z.-Y. Zhou, C.-M. Che, J. Am. Chem. Soc. 2001, 123, 4843-4844;
35. b) Y. Li, J.-S. Huang, Z.-Y. Zhou, C.-M. Che, X.-Z. You, J. Am. Chem. Soc. 2002, 124, 13185-13193;
36. c) S. Priya, M. S. Balakrishna, S. M. Mobin, R. McDonald, J. Organomet. Chem. 2003, 688, 227-235.
37. Although both the yield and selectivity were unsatisfactory, syntheses of 4c by ruthenium-and rhodium-catalyzed reactions of styrene with diphenyldiazoacetate have been reported; a) Ru: W. Baratta, W. A. Herrmann, R. M. Kratzer, P. Rigo, Organometallics 2000, 19, 3664-3669;
38. b) Rh: H. Werner, M. E. Schneider, M. Bosch, J. Wolf, J. H. Teuben, A. Meetsma, S. I. Troyanov, Chem. Eur. J. 2000, 6, 3052-3059.
39. M. P. Doyle, M. A. McKervey, T. Ye, in Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998.
40. N. Jeong in Modern Rhodium-Catalyzed Organic Reactions (Ed.: P. A. Evans), Wiley-VCH, Weinheim, 2005, pp. 215-240.
41. W. T. Brady, Synthesis 1971, 415-422.
42. J. A. Osborn, G. Wilkinson, Inorg. Synth. 1967, 10, 67-71.
43. N. Ahmad, J. J. Levison, S. D. Robinson, M. F. Uttley, Inorg. Synth. 1990, 28, 81-83.
44. R. Young, G. Wilkinson, Inorg. Synth. 1977, 17, 75-77.