Selective cine substitution of 1-arylethenyl acetates with arylboron reagents and a diene/rhodium catalyst

Angewandte Chemie - International Edition

Volumn 49, Issue 36, 2010, Pages 6396-6399

  Yu, Jung Yi ^a   Shimizu, Ryosuke ^a   Kuwano, Ryoichi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Acetates; Boranes; Homogeneous catalysis; Olefination; Rhodium

Indexed keywords

A-CARBON; ACETATES; ALKENYL; ARYLBORON; ARYLBORONIC ACIDS; BORANES; HOMOGENEOUS CATALYSIS; OLEFINATION;

CATALYSIS; CATALYSTS; HYDRIDES; REACTION KINETICS; RHODIUM;

BORON COMPOUNDS;

EID: 77956033162     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002745     Document Type: Article

References (28)

1. For a review, see: J. Suwiń ski, K. Świerczek, Tetrahedron 2001, 57, 1639.
2. For recent examples, see: C. Enguehard, H. Allouchi, A. Gueiffier, S. L. Buchwald, J. Org. Chem. 2003, 68, 5614
3. W. Kleist, S. S. Pröckl, M. Drees, K. Köhler, L. Djakovitch, J. Mol. Catal. A 2009, 303, 15.
4. K. Yoshida, T. Hayashi, J. Am. Chem. Soc. 2003, 125, 2872.
5. M. E. Limmert, A. H. Roy, J. F. Hartwig, J. Org. Chem. 2005, 70, 9364.
6. A. L. Hansen, J.-P. Ebran, T. M. Gøgsig, T. Skrydstrup, J. Org. Chem. 2007, 72, 6464.
7. A. T. Lindhardt, T. M. Gøgsig, T. Skrydstrup, J. Org. Chem. 2009, 74, 135
8. A. L. Hansen, J.-P. Ebran, M. Ahlquist, P.-O. Norrby, T. Skrydstrup, Angew. Chem. 2006, 118, 3427;
9. Angew. Chem. Int. Ed. 2006, 45, 3349
10. J.-P. Ebran, A. L. Hansen, T. M. Gøgsig, T. Skrydstrup, J. Am. Chem. Soc. 2007, 129, 6931.
11. For the electrophilic cine substitution of alkenylmetal substrates with aryl halides using a palladium catalyst, see: J. C. Anderson, S. Anguille, R. Bailey, Chem. Commun. 2002, 2018
12. E. Fillion, N. J. Taylor, J. Am. Chem. Soc. 2003, 125, 12700.
13. J.-Y. Yu, R. Kuwano, Angew. Chem. 2009, 121, 7353
14. Angew. Chem. Int. Ed. 2009, 48, 7217.
15. Separately, Kwong et al. reported the rhodium-catalyzed crosscoupling of vinyl acetate promptly after our report (see Ref. ]): H.W. Lee, F. Y. Kwong, Synlett 2009, 3151.
16. In general, compared to cod, the nbd ligand tightly binds to a transition metal with a small bite angle. The properties of nbd may be disadvantageous for the β-hydride elimination from C to afford the intermediate D in Scheme 2.
17. J. L. Butikofer, E. W. Kalberer, W. C. Schuster, D. M. Roddick, Acta Crystallogr. Sect. C 2004, 60, m353
18. H.-J. Drexler, S. Zhang, A. Sun, A. Spannenberg, A. Arrieta, A. Preetz, D. Heller, Tetrahedron: Asymmetry 2004, 15, 2139.
19. T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 2003, 125, 11508
20. C. Defieber, J.-F. Paquin, S. Serna, E. M. Carreira, Org. Lett. 2004, 6, 3873.
21. The additives, tert-amyl alcohol and diisopropylamine, may activate 2a through the interaction between the lone pair of the additives and the boron atom of 2a. Alternatively, the additives may assist 2a to dissolve in toluene.
22. The uses of the electron-deficient arylboronic acids, 2d, 2e, and 2 f, instead of their corresponding arylboronate, afforded the cine-substitution products 3d, 3e, and 3 f in 25%, 21%, and 19% yield, respectively. The use of electron-deficient arylboronic acid 2g did not afford any cine-substitution product (3g).
23. 2]-4a in a 92:8 molar ratio. The cine-substitution product (67%D) was isolated in 70% yield.
24. The kinetic studies of the rhodium-catalyzed 1,4-addition of phenylboronic acid to the enone indicated that the reaction between (hydroxo)rhodium(I) and the organoboron compound is the rate-determining step in the catalytic reaction and that the use of a diene ligand in place of bisphosphine causes the acceleration of the transmetalation step.
25. A. Kina, H. Iwamura, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 3904
26. A. Kina, Y. Yasuhara, T. Nishimura, H. Iwamura, T. Hayashi, Chem. Asian J. 2006, 1, 707
27. W.-L. Duan, H. Iwamura, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 2130.
28. In our previous report (see Ref. [8]), we concluded that the ipsosubstitution proceeded through the oxidative addition of vinyl acetate to bis(phosphine)-chelated rhodium(I). The chelation of the bis(phosphine) would be advantageous to the oxidative addition because it would increase the electron density on the rhodium.