Alkenylation of C-H bonds via reaction with vinyl and dienyl triflones. Stereospecific synthesis of trisubstituted vinyl triflones via organocopper addition to acetylenic triflones

Journal of the American Chemical Society

Volumn 118, Issue 47, 1996, Pages 11986-11987

  Xiang, Jason ^a   Fuchs, P L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029853621     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962790b     Document Type: Article

References (26)

1. Syntheses Via Vinyl Sulfones 68. Triflone Chemistry 7. For triflone paper 6, see ref 6.
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4. 3 = 107 kcal/mol: Handbook of Chemistry and Physics, 74th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton. FL, 1993-1994; pp 9-137.
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8. (d) Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1991, 32, 7525.
9. Xiang, J.; Fuchs, P. L. Tetrahedron Lett. 1996, 37, 5269.
10. Russell, G. A.; Ngoviwatchai, P. J. Org. Chem. 1989, 54, 1836 and references cited therein. This finding has recently been extended to the additions of o-alkoxy radicals to styryl sulfoximines (Clark, A. J.; Rooke, S.; Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909). For general references to olefin formation via β-sulfonyl radical chemistry, see: Ono N.; Kamimura, A.; Kaji, A. J. Org. Chem. 1987, 52, 5111 and references cited therein.
11. Russell, G. A.; Ngoviwatchai, P. J. Org. Chem. 1989, 54, 1836 and references cited therein. This finding has recently been extended to the additions of o-alkoxy radicals to styryl sulfoximines (Clark, A. J.; Rooke, S.; Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909). For general references to olefin formation via β-sulfonyl radical chemistry, see: Ono N.; Kamimura, A.; Kaji, A. J. Org. Chem. 1987, 52, 5111 and references cited therein.
12. Russell, G. A.; Ngoviwatchai, P. J. Org. Chem. 1989, 54, 1836 and references cited therein. This finding has recently been extended to the additions of o-alkoxy radicals to styryl sulfoximines (Clark, A. J.; Rooke, S.; Sparey, T. J.; Taylor, P. C. Tetrahedron Lett. 1996, 37, 909). For general references to olefin formation via β-sulfonyl radical chemistry, see: Ono N.; Kamimura, A.; Kaji, A. J. Org. Chem. 1987, 52, 5111 and references cited therein.
13. (a) Bertrand, M. P. Org. Prep. Proc. Int. 1994, 26, 257.
14. (b) Chatgilialoglu, C. Sulfonyl Radicals. In Chemistry of Sulphones and Sulphoxides; Patai, S., Ed.; John Wiley: New York, 1988; pp 1089-1113.
15. Mahadevan, A.; Fuchs, P. L. Tetrahedron Lett. 1994, 35, 6025.
16. This material was prepared by photochemical isomerization of E-14. See ref 12.
17. An alternative explanation would involve reversible addition of the THF radical, but this would require equilibration via breaking of C-C bonds and is deemed less likely until a definitive mechanistic study is undertaken.
18. Compounds shown in Scheme 6 were either recently prepared by the method of Xiang, Mahadevan, and Fuchs (J. Am. Chem. Soc. 1996, 118, 4284) or were prepared in an analogous fashion (see Supporting Information for synthesis and characterization of E-20a.)
19. Although alkylsulfonyl iodides undergo radical trans-addition to acetylenes to generate E-β-iodovinyl sulfones (Truce, W. E.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727. Short, K. M.; Ziegler, C. B., Jr. Tetrahedron Lett. 1993, 34, 71), fluorinated sulfonyl iodides also generate the E-β-iodovinyl perfluoroalkanes via competitive sulfur dioxide extrusion from the perfluorosulfonyl radical (ref 5c). These facts dictated the selection of a photochemical synthesis for compound E-27a.
20. Although alkylsulfonyl iodides undergo radical trans-addition to acetylenes to generate E-β-iodovinyl sulfones (Truce, W. E.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727. Short, K. M.; Ziegler, C. B., Jr. Tetrahedron Lett. 1993, 34, 71), fluorinated sulfonyl iodides also generate the E-β-iodovinyl perfluoroalkanes via competitive sulfur dioxide extrusion from the perfluorosulfonyl radical (ref 5c). These facts dictated the selection of a photochemical synthesis for compound E-27a.
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26. Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Org. Chem. 1979, 44, 1744. For a review, see: Yamamoto, Y. Angew, Chem., Int. Ed. Engl. 1986, 25, 947.