Palladium-catalyzed hydrophenylation of bicyclic alkenes

Tetrahedron

Volumn 58, Issue 47, 2002, Pages 9527-9540

  Mayo, Peter ^a   Tam, William ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Bicyclic alkenes; Chemoselectivity; Heck coupling; Hydrophenylation; Palladium; Regioselectivity; Stereoselectivity

Indexed keywords

NORBORNADIENE DERIVATIVE; NORBORNENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; HYDROPHENYLATION; ISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037131967     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01277-2     Document Type: Article

References (34)

1. For recent reviews, see: (a) Beletskaya I.P., Cheprakov A.V. Chem. Rev. 100:2000;3009. and references cited therein (b) Amatore C., Jutand A. Acc. Chem. Res. 33:2000;314.
2. (a) Larock R.C., Johnson P.L. J. Chem. Soc., Chem. Commun. 1989;1368 (b) Arcadi A., Marinelli F., Bernocchi E., Cacchi S., Ortar G. J. Organomet. Chem. 368:1989;249 (c) Clayton S.C., Regan A.C. Tetrahedron Lett. 34:1993;7493.
3. (a) Larock R.C., Babu S. Tetrahedron Lett. 28:1987;5291 (b) Burns B., Grigg R., Ratananukul P., Sridharan V., Stevenson P., Worakun T. Tetrahedron Lett. 29:1988;4329.
4. (a) Brunner H., Kramler K. Synthesis. 1991;1121 (b) Sakuraba S., Awano K., Achiwa K. Synlett. 1994;291 (c) Moinet C., Fiaud J.-C. Tetrahedron Lett. 36:1995;2051.
5. Ozawa F., Kobatake Y., Kubo A., Hayashi T. J. Chem. Soc., Chem. Commun. 1994;1323.
6. (a) Hay L.A., Koenig T.M., Ginah F.O., Copp J.D., Mitchell D. J. Org. Chem. 63:1998;5050 (b) Jia C., Piao D., Kitamura T., Fujiwara Y. J. Org. Chem. 65:2000;7516 (c) Jia C., Lu W., Oyamada J., Kitamura T., Matsuda K., Irie M., Fujiwara Y. J. Am. Chem. Soc. 122:2000;7252.
7. (a) Yip C., Handerson S., Jordan R., Tam W. Org. Lett. 1:1999;791 (b) Yip C., Handerson S., Tranmer G.K., Tam W. J. Org. Chem. 66:2001;276.
8. (a) Tranmer G.K., Keech P., Tam W. Chem. Commun. 2000;863 (b) Tranmer G.K., Tam W. J. Org. Chem. 66:2001;5113.
9. (a) Mayo P., Poirier M., Rainey J., Tam W. Tetrahedron Lett. 40:1999;7727 (b) Mayo P., Orlova G., Goddard J.D., Tam W. J. Org. Chem. 66:2001;5182.
10. Tranmer G.K., Yip C., Handerson S., Jordan R.W., Tam W. Can. J. Chem. 78:2000;527.
11. (a) Jordan R.W., Tam W. Org. Lett. 2:2000;3031 (b) Jordan R.W., Tam W. Org. Lett. 3:2001;2367.
12. Mayo P., Hecnar T., Tam W. Tetrahedron. 57:2001;5931.
13. Mayo P., Tam W. Tetrahedron. 57:2001;5943.
14. Trost B.M., Balkovec J.M., Angle S.R. Tetrahedron Lett. 27:1986;1445.
15. Schore N.E. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;721 Pergamon, Oxford.
16. Morisaki Y., Kondo T., Mitsudo T. Org. Lett. 2:2000;949.
17. Michieletto I., Fabris F., De Lucchi O. Tetrahedron: Asymmetry. 11:2000;2835.
18. b. These dihedral angles were then compared to the Karplus curve for the determination of the theoretical coupling constants.
19. Similar methods have been used for the assignment of exo and endo stereochemistry of bicyclic alkanes, see: (a) Flautt T.J., Erman W.F. J. Am. Chem. Soc. 85:1963;3212 (b) Mazzocchi P.H., Stahly B., Dodd J., Rondan N.G., Domelsmith L.N., Rozeboom M.D., Caramella P., Houk K.N. J. Am. Chem. Soc. 102:1980;6482. See also Refs. 8b,12,13.
20. Cossu S., De Lucchi O., Paulon A., Peluso P., Zonta C. Tetrahedron Lett. 42:2001;3515.
21. For recent reviews, see: (a) Cieplak A.S. Chem. Rev. 99:1999;1265 (b) Ohwada T. Chem. Rev. 99:1999;1337 (c) Mehta G., Chandrasekhar J. Chem. Rev. 99:1999;1437.
22. MacWhorter S.E., Sampath V., Olmstead M.M., Schore N.E. J. Org. Chem. 53:1988;203.
23. Lautens M., Tam W., Edwards L.G. J. Chem. Soc., Perkin Trans. 1. 1994;2143.
24. Mayo P., Tam W. Tetrahedron. 58:2002;9513-9525.
25. b. These dihedral angles were then compared to the Karplus curve for the determination of the theoretical coupling constants.
26. GOESY: Gradient enhanced nuclear Overhauser enhancement spectroscopy, see: (a) Stonehouse J., Adell P., Keeler J., Shaka A.J. J. Am. Chem. Soc. 116:1994;6037 (b) Stott K., Stonehouse J., Keeler J., Hwang T.-L., Shaka A.J. J. Am. Chem. Soc. 117:1995;4199 (c) Dixon A.M., Widmalm G., Bull T.E. J. Magn. Reson. 147:2000;266.
27. Still W.C., Kahn M., Mitra A. J. Org. Chem. 43:1978;2923.
28. Lautens M., Edwards L.G., Tam W., Lough A.J. J. Am. Chem. Soc. 117:1995;10276.
29. Verkruijsse H.D., Brandsma L. Recl. Trav. Chim. Pays-Bas. 105:1986;66.
30. Gassman P.G., Mansfield K.T. J. Am. Chem. Soc. 90:1968;1517.
31. Rousseau G., Le Perchec P., Conia J.M. Synthesis. 1978;67.
32. (a) Cossu S., De Lucchi O., Paulon A., Peluso P., Zonta C. Tetrahedron Lett. 42:2001;3515 (b) Gassman P.G., Gennick I. J. Org. Chem. 45:1980;5211.
33. Gassman P.G., Gennick I. J. Org. Chem. 45:1980;5211.
34. Kleinfelter D.C., Dye T.E., Mallory J.E., Trent E.S. J. Org. Chem. 32:1967;1734.