On the regiochemistry of nucleophilic attack on 2-halo π-allyl complexes. Part 3: The electronic effect of phenoxide ion and the ligand

Tetrahedron Letters

Volumn 43, Issue 49, 2002, Pages 8989-8992

  Organ, Michael G ^a   Arvanitis, Elena A ^a   Hynes, Stephen J ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CARBON; LIGAND; MALONIC ACID; OXIDE; PALLADIUM; PROPYLENE;

ARTICLE; CATALYST; CYCLOADDITION; IONIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037010812     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02183-4     Document Type: Article

References (14)

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7. Simple allylic substrates have been alkylated at the central carbon leading to cyclopropane formation via reductive elimination of the intermediate metallacyclobutane, see: (a) Hegedus, L. S.; Darlington, W. H.; Russel, C. E. J. Org. Chem. 1980, 45, 5193-5196; (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem. Int. Ed. Engl. 1992, 31, 234-236; © Carfagna, C.; Galarini, R.; Musco, A. J. Mol. Catal. 1992, 72, 19-27; (d) Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 6420-6422.
8. Simple allylic substrates have been alkylated at the central carbon leading to cyclopropane formation via reductive elimination of the intermediate metallacyclobutane, see: (a) Hegedus, L. S.; Darlington, W. H.; Russel, C. E. J. Org. Chem. 1980, 45, 5193-5196; (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem. Int. Ed. Engl. 1992, 31, 234-236; © Carfagna, C.; Galarini, R.; Musco, A. J. Mol. Catal. 1992, 72, 19-27; (d) Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 6420-6422.
9. Simple allylic substrates have been alkylated at the central carbon leading to cyclopropane formation via reductive elimination of the intermediate metallacyclobutane, see: (a) Hegedus, L. S.; Darlington, W. H.; Russel, C. E. J. Org. Chem. 1980, 45, 5193-5196; (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem. Int. Ed. Engl. 1992, 31, 234-236; © Carfagna, C.; Galarini, R.; Musco, A. J. Mol. Catal. 1992, 72, 19-27; (d) Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 6420-6422.
10. Simple allylic substrates have been alkylated at the central carbon leading to cyclopropane formation via reductive elimination of the intermediate metallacyclobutane, see: (a) Hegedus, L. S.; Darlington, W. H.; Russel, C. E. J. Org. Chem. 1980, 45, 5193-5196; (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem. Int. Ed. Engl. 1992, 31, 234-236; © Carfagna, C.; Galarini, R.; Musco, A. J. Mol. Catal. 1992, 72, 19-27; (d) Tjaden, E. B.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 6420-6422.
11. Castano A.M., Aranyos A., Szabó K.J., Bäckvall J.-E. Angew. Chem. Int. Ed. Engl. 34:1995;2551-2553.
12. Aranyos A., Szabó K.J., Castano A.M., Bäckvall J.-E. Organometallics. 16:1997;1058-1064.
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14. Trost B.M., Organ M.G. J. Am. Chem. Soc. 116:1994;10320-10321.