"β-cis-SAr effect" on decarbonylation from α,β-unsaturated acyl and aroyl complexes

Chemical Communications

Volumn , Issue 8, 2006, Pages 868-870

  Kato, Tomohiro ^a   Kuniyasu, Hitoshi ^a   Kajiura, Takamichi ^a   Minami, Yasunori ^a   Ohtaka, Atsushi ^a   Kinomoto, Masanori ^a   Terao, Jun ^a   Kurosawa, Hideo ^a   Kambe, Nobuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX;

ARTICLE; ATOM; CATALYSIS; CHEMICAL MODIFICATION; DECARBONYLATION; STOICHIOMETRY;

EID: 32844470775     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b515616e     Document Type: Article

References (28)

1. (a) M. C. Whisler, S. MacNeil, V. Snieckus and P. Beak, Augew. Chem., Int. Ed., 2004, 43, 2206;
2. (b) P. Beak, A. Basu, D. J. Gallagher, Y. S. Park and S. Thayumanavan, Acc. Chem. Res., 1996, 29, 552;
3. (c) V. Snieckus, Chem. Rev., 1990, 90, 879;
4. (d) P. Beak and A. I. Meyers, Acc. Chem. Res., 1986, 19, 356;
5. (e) A. H. Hoveyda, D. A. Evans and G. C. Fu, Chem. Rev., 1993, 93, 1307.
6. For reviews of oxidative addition, see: (a) M. Albrecht and G. van Koten, Angew. Chem., Int. Ed., 2001, 40, 3750;
7. (b) M. E. van der Boom and D. Milstein, Chem. Rev., 2003, 103, 1759;
8. (c) V. Ritleng, C. Sirlin and M. Pfeffer, Chem. Rev., 2002, 102, 1731;
9. (d) F. Kakiuchi and N. Chatani, Adv. Synth. Catal., 2003, 345, 1077.
10. H. Kuniyasu, T. Kato, Y. Minami, J. Terao and N. Kambe, Organometallics, submitted.
11. H. Kuniyasu, A. Ohtaka, M. Kinomoto and H. Kurosawa, J. Am. Chem. Soc., 2000, 122, 2375.
12. 2 gas bubbling was also efficient for decarbonylation to yield 4a selectively in good yield.
13. S. P. Dent, C. Eaborn and A. Pidcock, J. Organomet. Chem., 1975, 97, 307.
14. 4Me-p groups are incorrectly oriented.
15. 3, C(O)OMe) have been formed by cycloaddition reactions, see: (a) M. M. Kubicki, R. Kergoat, H. Scordia, L. C. Gomes de Lima, J. E. Guerchais and P. L'Haridon, J. Organomet. Chem., 1988, 340, 41;
16. (b) M. M. Kubicki, L. C. Gomes de Lima, H. Scordia, J. E. Guerchais and P. L'Haridon, J. Organomet. Chem., 1989, 367, 143;
17. (c) L. Carlton, J. L. Davidson and M. Shiralian, J. Chem. Soc., Dalton Trans., 1986, 1577;
18. (d) P. Veya, C. Floriani, A. Chiesi-Villa and C. Rizolli, Organometallics, 1993, 12, 4646;
19. (e) S. Lee, K. Cheung and W. Wong, J. Organomet. Chem., 1995, 494, 273 and references therein.
20. 3-ligated Pt(II)-complexes were ranging about >3500 Hz, 2700-3100 Hz and 1500-1800 Hz, respectively. G. K. Anderson and R. J. Cross, J. Chem. Soc., Dalton Trans., 1980, 1434. See also ref. 3 and 4.
21. M. Gerisch, F. W. Heinemann, C. Bruhn, J. Scholz and D. Steinborn, Organometallics, 1999, 18, 564.
22. 3 (1.5 equiv.) taken at -70°C and -50 °C detected mixtures of trans-3a/6a in the ratios of 56:44 and 8:92, respectively. See the ESI for more details.
23. There can be two possible mechanisms. One is the migration of the vinyl moiety to a vacant coordination site of Pt(II)-complex 6a and the other is a coplanar slippage of vinyl carbon to the β-cis-SAr coordination site with the C-S bond gradually cleaved.
24. Meyer et al. have recently proposed that a similar coordination by SeAr to Pd promoted the carbonylation of vinylpalladium. (a) D. J. Knapton and T. Y. Meyer, J. Org. Chem., 2005, 70, 785;
25. (b) D. J. Knapton and T. Y. Meyer, Org. Lett., 2004, 6, 687.
26. K. Osakada, T. Yamamoto and A. Yamamoto, Tetrahedron Lett., 1987, 28, 6321.
27. H. Kuniyasu and H. Kurosawa, Chem.-Eur. J., 2002, 8, 2669.
28. L. L. Hegedus and R. W. McCabe, Catalyst Poisoning, Marcel Dekker, New York, 1984.