Density Functional Study on the Regioselectivity of Nucleophilic Attack in 1,3-Disubstituted (Diphosphino)(η3-allyl)palladium Cations

Organometallics

Volumn 18, Issue 24, 1999, Pages 4934-4941

  Branchadell, Vicenç ^a   Moreno Mañas, Marcial ^a   Pajuelo, Francesca ^a   Pleixats, Roser ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001273646     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990371s     Document Type: Article

References (104)

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2. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
3. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
4. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
5. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
6. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
7. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
8. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
9. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
10. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
11. For reviews see: (a) Trost, B. M.; Verhoeven, T. R. Organopalladium Compounds in Organic Synthesis and in Catalysis. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 8, Chapter 57. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (c) Trost, B. M. Chemtracts-Org. Chem. 1988, 1, 415. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (e) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140. (g) Tsuji, J. Tetrahedron 1986, 42, 4361. (h) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985. (i) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257. (j) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089. (k) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995. (l) Harrington, P. J. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2. (m) Moreno-Mañas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
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