Palladium-mediated fragmentation of meta photocycloadducts using carbon based electrophiles. Part 1

Tetrahedron

Volumn 62, Issue 14, 2006, Pages 3423-3434

  Penkett, Clive S ^a   Sims, Rupert O ^a   Byrne, Paul W ^b   Kingston, Lee ^c   French, Richard ^a   Dray, Lauriane ^a   Berritt, Simon ^a   Lai, Jason ^a   Avent, Anthony G ^a   Hitchcock, Peter B ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

^b Langford House   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

Allylsilane formation; Atom efficiency; Heck reaction; Palladium; Photoaddition; Tandem reaction

Indexed keywords

1 IODO 2 NITROBENZENE; ALKENE; ANISOLE; BENZENE; BICYCLO COMPOUND; BRIDGED COMPOUND; CARBON; CYCLOHEXANE; ETHER DERIVATIVE; NITROBENZENE DERIVATIVE; PALLADIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; FRAGMENTATION REACTION; HECK REACTION; MODEL; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33644916455     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.042     Document Type: Article

References (29)

1. K.E. Wilzbach, and L. Kaplan J. Am. Chem. Soc. 88 1966 2066
2. D. Bryce-Smith, A. Gilbert, and B.H. Orger J. Chem. Soc., Chem. Commun. 1966 512
3. J. Cornelisse Chem. Rev. 93 1993 615
4. P.A. Wender, L. Siggel, and J.M. Nuss A. Padwa Organic Photochemistry Vol. 10 1989 Marcel-Dekker New York Chapter 4
5. P.A. Wender, L. Siggel, and J.M. Nuss B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 645
6. P.A. Wender, R. Ternansky, M. de Long, S. Singh, A. Olivero, and K. Rice Pure Appl. Chem. 62 1990 1597
7. D. De Keukeleire, and S.-L. He Chem. Rev. 93 1993 359
8. P.A. Wender, and R.J. Ternansky Tetrahedron Lett. 26 1985 2625
9. P.A. Wender, and J.J. Howbert Tetrahedron Lett. 24 1983 5325
10. R. Srinivasan, V.Y. Merritt, and G. Subrahmanyam Tetrahedron Lett. 15 1974 2715
11. P.A. Wender, and J.J. Howbert J. Am. Chem. Soc. 103 1981 688
12. A.G. Avent, P.W. Byrne, and C.S. Penkett Org. Lett. 1 1999 2073
13. C.S. Penkett, R.O. Sims, R. French, L. Dray, S.J. Roome, and P.B. Hitchcock Chem. Commun. 2004 1932
14. A. de Meijere, and F.E. Meyer Angew. Chem., Int. Ed. Engl. 33 1995 2379
15. S.E. Gibson, and R.J. Middleton Contemp. Org. Synth. 3 1996 447
16. G.T. Crisp Chem. Soc. Rev. 27 1998 427
17. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
18. G. Poli, G. Giambastiani, and A. Heumann Tetrahedron 56 2000 5959
19. J.T. Link Organic Reactions Vol. 60 2002 Wiley Hoboken, NJ Chapter 2
20. A.B. Dounay, and L.E. Overman Chem. Rev. 103 2003 2945
21. We thank Mark Charles, DPhil thesis, University of Sussex, 2003 for suggesting these initial reaction conditions.
22. 5 Unit cell parameters: a 9.1079(17) b 12.352(2) c 13.656(2) Å beta 107.32°space group P21/n.
23. C.S. Penkett, P.W. Byrne, B.J. Teobald, B. Rola, A. Ozanne, and P.B. Hitchcock Tetrahedron 60 2004 2771
24. H. Lin, and S.J. Danishefsky Angew. Chem., Int. Ed. 42 2003 36
25. W. Cabri, and I. Candiani Acc. Chem. Res. 28 1995 2
26. D. Wilhelm, J.E. Bäckvall, R.E. Nordberg, and T. Norin Organometallics 4 1985 1296
27. C. Clarke, I. Fleming, J.M.D. Fortunak, P.T. Gallagher, M.C. Honan, A. Mann, C.O. Nübling, P.R. Raithby, and J.J. Wolff Tetrahedron 44 1988 3931
28. M. Gilman J. Am. Chem. Soc. 71 1949 2066
29. A. Ashimori, T. Matsuura, L.E. Overman, and D.J. Poon J. Org. Chem. 58 1993 6949