Phosphinic Acid Induced Reversal of Regioselectivity in Pd-Catalyzed Hydrophosphinylation of Alkynes with Ph2P(O)H

Angewandte Chemie - International Edition

Volumn 37, Issue 1-2, 1998, Pages 94-96

  Han, Li Biao ^a   Hua, Ruimao ^a   Tanaka, Masato ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

Alkynes; Homogeneous catalysis; Palladium; Phosphorus; Regioselectivity

Indexed keywords

EID: 0031930454     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980202)37:1/2<94::aid-anie94>3.0.co;2-t     Document Type: Article

References (22)

1. For partial reversal of the regioselectivity in hydrosilylation, see a) K. H. Pannell, J. Rozell, J. Lu, S.-Y. Tien-Mayr, Organometallics 1988, 7, 2524; b) M. Rivera-Claudio, J. Rozell, I.E. Ramirez-Oliva, J. Cervantes, K. H. Pannell, J. Organomet. Chem. 1996, 521, 267.
2. For partial reversal of the regioselectivity in hydrosilylation, see a) K. H. Pannell, J. Rozell, J. Lu, S.-Y. Tien-Mayr, Organometallics 1988, 7, 2524; b) M. Rivera-Claudio, J. Rozell, I.E. Ramirez-Oliva, J. Cervantes, K. H. Pannell, J. Organomet. Chem. 1996, 521, 267.
3. L.-B. Han, N. Choi, M. Tanaka, Organometallics 1996, 15, 3259.
4. a) Handbook of Organophosphorus Chemistry (Ed.: R. Engel), Marcel Dekker, New York, 1992;
5. b) C. R. Johnson, T. Imamoto, J. Org. Chem. 1987, 52, 2170:
6. c) K. M. Pietrusiewicz, M. Zablocka, W. Wisniewski, Phosphorus. Sulfur Silicon Relat. Elem. 1990, 49-50, 263;
7. d) K. M. Pietrusiewiczm, W. Wisniewski, M. Zablocka, Tetrahedron 1989, 45, 337;
8. e) K., M. Pietrusiewicz, M. Zablocka, Tetrahedron Lett. 1988, 20, 1991;
9. f) H. Brunner, S. Limmer, J. Organomet. Chem. 1991, 417, 173;
10. g) J. Berlan, J.-P. Battioni, K. Koosha. Tetrahedron Lett. 1976, 3351;
11. h) K. M. Pictrusiewicz, M. Zablocka, ibid. 1988, 29, 937:
12. i) A. Brandi, S. Cicchi, A. Goli. ibid. 1991, 32, 3265.
13. In the absence of the catalyst, neither la nor 2a was obtained under the same conditions.
14. 2P(O)OH (Table 1) and reheated at 70°C for 2 h.
15. Secondary phosphane oxides exist in two lautomeric forms, P(=O)H and P-OH; the former is dominant in the equilibrium: a) W. J. Bailey, R. B. Fox, J. Org. Chem. 1963, 28, 531; b) W. J. Bailey, R. B. Fox, ibid. 1964, 29, 1013; L. A. Hamilton, P. S. Landis in Organic Phosphorus Compounds. Vol. 4 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, chap. 11.
16. Secondary phosphane oxides exist in two lautomeric forms, P(=O)H and P-OH; the former is dominant in the equilibrium: a) W. J. Bailey, R. B. Fox, J. Org. Chem. 1963, 28, 531; b) W. J. Bailey, R. B. Fox, ibid. 1964, 29, 1013; L. A. Hamilton, P. S. Landis in Organic Phosphorus Compounds. Vol. 4 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, chap. 11.
17. Secondary phosphane oxides exist in two lautomeric forms, P(=O)H and P-OH; the former is dominant in the equilibrium: a) W. J. Bailey, R. B. Fox, J. Org. Chem. 1963, 28, 531; b) W. J. Bailey, R. B. Fox, ibid. 1964, 29, 1013; L. A. Hamilton, P. S. Landis in Organic Phosphorus Compounds. Vol. 4 (Eds.: G. M. Kosolapoff, L. Maier), Wiley, New York, 1972, chap. 11.
18. 2P(O)OH proceeds by hydropalladation; see ref. [2].
19. a) Y.-J. Kim, K. Osakada, A. Takenaka, A. Yamamoto, J. Am. Chem. Soc. 1990, 112, 1096;
20. b) F. Kawataka, Y. Kayaki, I. Shimizu, A. Yamamoto, Organometallics 1994, 13, 3517.
21. 2P(O)OH even upon heating at 70°C for 2 h.
22. 2P(O)OH.