Rhodium-catalyzed regioselective olefin hydrophosphorylation

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4303-4306

  Reichwein, John F ^a   Patel, Mittun C ^a   Pagenkopf, Brian L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

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ARTICLE;

EID: 0001612690     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016989r     Document Type: Article

References (27)

1. For a review, see: Fields, S. C. Tetrahedron 1999, 55, 12237-12273.
2. For a review, see: Blackburn, M. G. Chem. Ind. (London) 1981, 134-144.
3. For reviews, see: (a) Eckstein, F.; Thomson, J. B. Methods Enzymol. 1995, 262, 189-202.
4. (b) Egli, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1894-1909.
5. (c) De Clercq, E. Biomed. Pharmacother. 1996, 50, 207-215.
6. For a review, see: Failla, S.; Finocchiaro, P.; Consiglio, G. A. Heteroat. Chem. 2000, 11, 493-504. For a recent report: Rushing, S. D.; Hammer, R. P. J. Am. Chem. Soc. 2001, 123, 4861-4862.
7. For a review, see: Failla, S.; Finocchiaro, P.; Consiglio, G. A. Heteroat. Chem. 2000, 11, 493-504. For a recent report: Rushing, S. D.; Hammer, R. P. J. Am. Chem. Soc. 2001, 123, 4861-4862.
8. Kafarski P.; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Prod. 1991, 63, 193-215.
9. For a review, see: Krise, J. P.; Stella, V. J. Adv. Drug Delivery Rev. 1996, 19, 287-310.
10. (a) Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1972.
11. (b) Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992.
12. (c) Corbridge, D. E. C. Phosphorus: An Outline of Its Chemistry, Biochemistry and Uses, 5th ed.; Elsevier: Amsterdam, 1995.
13. Han, L.-B.; Mirzaei, F.; Zhao, C-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407-5408.
14. Radical olefin hydrophosphorylation is known: Stiles, A. R.; Vaughan, W. E.; Rust, F. F. J. Am. Chem. Soc. 1958, 80, 714-716.
15. Alkyne hydrophosphorylation was reported previously, see: (a) Han, L.-B.; Zhao, C.-Q.; Tanaka, M. J. Org. Chem. 2001, 66, 5929-5932.
16. (b) Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 94-96.
17. (c) Han, L.-B.; Choi, N. R.; Tanaka, M. Organometallics 1996, 15, 3259-3261.
18. (d) Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem., Int. Ed. 2001, 40, 1929-1932.
19. de Graaf, W.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1989, 8, 2907-2917.
20. 2 failed in the reaction. Details will be described elsewhere.
21. Similar results have been observed; see ref 8.
22. Although reactions were typically assembled in an inert atmosphere glovebox, the use of Wilkinson's catalyst that had been stored exposed to air for weeks performed equally well provided 2 equiv of DPPB per Rh was added to the reaction.
23. The reaction mixture was yellow throughout the initial period of the reaction but turned orange/brown before complete consumption of phosphonate 1 (85% yield from one-half of the reaction). After 2 mol % additional DPPB was added to the reaction, the yellow color returned and the reaction proceeded to completion.
24. 3RhCl, 5 mol % DPPB, and dioxane (0.25 M). The reaction mixture was heated at 100 °C for 20 h and then concentrated in vacuo. The phosphonates were purified by flash chromatography on silica gel.
25. 16 This gave rather disappointing results, but by increasing both the catalyst loading and the reaction time (2 d) a 70% yield of the β-benzyloxy phosphonate 26 was obtained. (Matrix Presented)
26. Palladium-catalyzed hydrophosphorylation of dienes has been reported: Miraei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2001, 42, 297-299.
27. The use of pinacol-derived phosphonates in Horner-like coupling reactions will be described elsewhere.