Carbophosphinylation of arynes with cyanomethyldiphenylphosphine oxide

Chemistry Letters

Volumn 34, Issue 11, 2005, Pages 1538-1539

  Yoshida, Hiroto ^a   Watanabe, Masahiko ^a   Ohshita, Joji ^a   Kunai, Atsutaka ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31544449751     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1538     Document Type: Article

References (25)

1. H. Yoshida and A. Kunai, J. Synth. Org. Chem. Jpn., 63, 627 (2005).
2. Si-Si: H. Yoshida, J. Ikadai, M. Shudo, J. Ohshita, and A. Kunai, J. Am. Chem. Soc., 125, 6638 (2003);
3. H. Yoshida, J. Ikadai, M. Shudo, J. Ohshita, and A. Kunai, Organometallics, 24, 156 (2005);
4. J. Ikadai, H. Yoshida, J. Ohshita, and A. Kunai, Chem. Lett., 34, 56 (2005);
5. Sn-Sn: H. Yoshida, K. Tanino, J. Ohshita, and A. Kunai, Angew. Chem., Int. Ed., 43, 5052 (2004);
6. S-Sn: H. Yoshida, T. Terayama, J. Ohshita, and A. Kunai, Chem. Commun., 2004, 1980;
7. N-Si: H. Yoshida, T. Minabe, J. Ohshita, and A. Kunai, Chem. Commun., 2005, 3454;
8. Se-Se and Te-Te: N. Petragnani and V. G. Toscano, Chem. Ber., 103, 1652 (1970);
9. S-S: J. Nakayama, T. Tajiri, and M. Hoshino, Bull. Chem. Soc. Jpn., 59, 2907 (1986).
10. C-Sn: H. Yoshida, Y. Honda, E. Shirakawa, and T. Hiyama, Chem. Commun., 2001, 1880;
11. C-N: H. Yoshida, E. Shirakawa, Y. Honda, and T. Hiyama, Angew. Chem., Int. Ed., 41, 3247 (2002);
12. C-Si: Y. Sato, Y. Kobayashi, M. Sugiura, and H. Shirai, J. Org. Chem., 43, 199 (1978).
13. H. Yoshida, M. Watanabe, J. Ohshita, and A. Kunai, Chem. Commun., 2005, 3292.
14. Addition of a carbon-carbon σ-bond of β-ketoesters to arynes has been reported: U. K. Tambar and B. M. Stoltz, J. Am. Chem. Soc., 127, 5340 (2005).
15. H. Yoshida, M. Watanabe, J. Ohshita, and A. Kunai, Tetrahedron Lett., 46, 6729 (2005).
16. Addition of a carbon-phosphorus σ-bond of phosphorus ylides to arynes has been reported: E. Zbiral, Tetrahedron Lett., 1964, 3963.
17. Y. Himeshima, T. Sonoda, and H. Kobayashi, Chem. Lett., 1983, 1211.
18. To a THF solution (1.0 mL) of 1 (0.40 mmol), 2a (0.20 mmol), and 18-Crown-6 (0.212 g, 0.80 mmol) was added KF (0.047 g, 0.80 mmol), and the reaction mixture was stirred at room temperature for the time specified in Scheme 1. The mixture was diluted with ethyl acetate, washed with brine and concentrated. The residue was purified by GPC to give the corresponding product.
19. Configuration of 3fa was determined based on coupling constants between aromatic proton and phosphorus as follows.
20. A significant amount of 2a was recovered in the reactions with low product yields (51% in the reaction using 1e, for example), and trace amounts of unidentified by-products were observed.
21. In the present reaction, consumption of aryne precursors was considerably slower than that in the reactions using β-dicarbonyl or α-cyanocarbonyl compounds, which resulted in the prolonged reaction time, although the reasons for this are unclear.
22. For a review on the nucleophilic couplings with arynes, see: S. V. Kessar, "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Flemming, Pergamon Press, Oxford (1991), Vol. 4, pp 483-515.
23. At present, the reasons why the nucleophilic substitution did not occur at the cyano moiety are unclear. For insertion into a methylene-cyano σ-bond by the reaction of arynes with lithiated acetonitrile derivatives, see: A. I. Meyers and P. D. Panesgrau, Tetrahedron Lett., 25, 2941 (1984);
24. S. P. Khanapure, L. Crenshaw, R. T. Reddy, and E. R. Biehl, J. Org. Chem., 53, 4915 (1988);
25. J. H. Waggenspack, L. Tran, S. Taylor, L. K. Yeung, M. Morgan, A. R. Deshmukh, S. P. Khanapure, and E. R. Biehl, Synthesis, 1992, 765.