Allylic Amination of Unactivated Olefins by Nitroarenes, Catalyzed by Ruthenium Complexes. A Reaction Involving an Intermolecular C-H Functionalization

Organometallics

Volumn 18, Issue 5, 1999, Pages 928-942

  Ragaini, Fabio ^a   Cenini, Sergio ^a   Tollari, Stefano ^a   Tummolillo, Giovanni ^a   Beltrami, Raffaella ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001491863     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980843n     Document Type: Article

References (113)

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34. (a) Bassoli, A.; Rindone, B.; Cenini, S. J. Mol. Catal. 1991, 66, 163. (b) Bassoli, A.; Rindone, B.; Tollari, S.; Cenini, S.; Crotti, C. J. Mol. Catal 1990, 60, 155.
35. 16 /pyridine, Iqbal included in a table on the different reactions effected an entry on the reaction between a nitro compound and an olefin to yield an aziridine. However, in the text, the section dealing with the reactions of acetylenes begins clearly stating that "olefins failed to undergo any reaction": Iqbal, A. F. M. CHEMTECH 1974, 566.
36. Intramolecular reactions of a nitro group and an olefin under CO pressure have already been reported by us and others to afford several types of heterocycles. However, in this case, the attack occurs at an olefin, rather than allylic carbon. For some examples see: (a) Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Publishers: Dordrecht, 1997; Chapter 5, and references therein, (b) Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S. J. Chem. Soc., Chem. Commun. 1986, 784. Crotti, C.; Cenini, S.; Todeschini, R.; Tollari, S. J. Chem. Soc., Faraday Trans. 1991, 87, 2811. Akazone, M.; Kondo, T.; Watanabe, Y. Chem. Lett. 1992, 769. (e) Tollari, S.; Cenini, S.; Crotti, C.; Giannella, E. J. Mol. Catal. 1994, 87, 203. (f) Tollari, S.; Cenini, S.; Ragaini, F.; Cassar, L. J. Chem. Soc., Chem. Commun. 1994, 1741. (g) Annunziata, R.; Cenini, S.; Palmisano, G.; Tollari, S. Synth. Commun. 1996, 26, 495.
37. Intramolecular reactions of a nitro group and an olefin under CO pressure have already been reported by us and others to afford several types of heterocycles. However, in this case, the attack occurs at an olefin, rather than allylic carbon. For some examples see: (a) Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Publishers: Dordrecht, 1997; Chapter 5, and references therein, (b) Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S. J. Chem. Soc., Chem. Commun. 1986, 784. Crotti, C.; Cenini, S.; Todeschini, R.; Tollari, S. J. Chem. Soc., Faraday Trans. 1991, 87, 2811. Akazone, M.; Kondo, T.; Watanabe, Y. Chem. Lett. 1992, 769. (e) Tollari, S.; Cenini, S.; Crotti, C.; Giannella, E. J. Mol. Catal. 1994, 87, 203. (f) Tollari, S.; Cenini, S.; Ragaini, F.; Cassar, L. J. Chem. Soc., Chem. Commun. 1994, 1741. (g) Annunziata, R.; Cenini, S.; Palmisano, G.; Tollari, S. Synth. Commun. 1996, 26, 495.
38. Intramolecular reactions of a nitro group and an olefin under CO pressure have already been reported by us and others to afford several types of heterocycles. However, in this case, the attack occurs at an olefin, rather than allylic carbon. For some examples see: (a) Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Publishers: Dordrecht, 1997; Chapter 5, and references therein, (b) Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S. J. Chem. Soc., Chem. Commun. 1986, 784. Crotti, C.; Cenini, S.; Todeschini, R.; Tollari, S. J. Chem. Soc., Faraday Trans. 1991, 87, 2811. Akazone, M.; Kondo, T.; Watanabe, Y. Chem. Lett. 1992, 769. (e) Tollari, S.; Cenini, S.; Crotti, C.; Giannella, E. J. Mol. Catal. 1994, 87, 203. (f) Tollari, S.; Cenini, S.; Ragaini, F.; Cassar, L. J. Chem. Soc., Chem. Commun. 1994, 1741. (g) Annunziata, R.; Cenini, S.; Palmisano, G.; Tollari, S. Synth. Commun. 1996, 26, 495.
39. Intramolecular reactions of a nitro group and an olefin under CO pressure have already been reported by us and others to afford several types of heterocycles. However, in this case, the attack occurs at an olefin, rather than allylic carbon. For some examples see: (a) Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Publishers: Dordrecht, 1997; Chapter 5, and references therein, (b) Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S. J. Chem. Soc., Chem. Commun. 1986, 784. Crotti, C.; Cenini, S.; Todeschini, R.; Tollari, S. J. Chem. Soc., Faraday Trans. 1991, 87, 2811. Akazone, M.; Kondo, T.; Watanabe, Y. Chem. Lett. 1992, 769. (e) Tollari, S.; Cenini, S.; Crotti, C.; Giannella, E. J. Mol. Catal. 1994, 87, 203. (f) Tollari, S.; Cenini, S.; Ragaini, F.; Cassar, L. J. Chem. Soc., Chem. Commun. 1994, 1741. (g) Annunziata, R.; Cenini, S.; Palmisano, G.; Tollari, S. Synth. Commun. 1996, 26, 495.
40. Intramolecular reactions of a nitro group and an olefin under CO pressure have already been reported by us and others to afford several types of heterocycles. However, in this case, the attack occurs at an olefin, rather than allylic carbon. For some examples see: (a) Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Publishers: Dordrecht, 1997; Chapter 5, and references therein, (b) Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S. J. Chem. Soc., Chem. Commun. 1986, 784. Crotti, C.; Cenini, S.; Todeschini, R.; Tollari, S. J. Chem. Soc., Faraday Trans. 1991, 87, 2811. Akazone, M.; Kondo, T.; Watanabe, Y. Chem. Lett. 1992, 769. (e) Tollari, S.; Cenini, S.; Crotti, C.; Giannella, E. J. Mol. Catal. 1994, 87, 203. (f) Tollari, S.; Cenini, S.; Ragaini, F.; Cassar, L. J. Chem. Soc., Chem. Commun. 1994, 1741. (g) Annunziata, R.; Cenini, S.; Palmisano, G.; Tollari, S. Synth. Commun. 1996, 26, 495.
41. Intramolecular reactions of a nitro group and an olefin under CO pressure have already been reported by us and others to afford several types of heterocycles. However, in this case, the attack occurs at an olefin, rather than allylic carbon. For some examples see: (a) Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Publishers: Dordrecht, 1997; Chapter 5, and references therein, (b) Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S. J. Chem. Soc., Chem. Commun. 1986, 784. Crotti, C.; Cenini, S.; Todeschini, R.; Tollari, S. J. Chem. Soc., Faraday Trans. 1991, 87, 2811. Akazone, M.; Kondo, T.; Watanabe, Y. Chem. Lett. 1992, 769. (e) Tollari, S.; Cenini, S.; Crotti, C.; Giannella, E. J. Mol. Catal. 1994, 87, 203. (f) Tollari, S.; Cenini, S.; Ragaini, F.; Cassar, L. J. Chem. Soc., Chem. Commun. 1994, 1741. (g) Annunziata, R.; Cenini, S.; Palmisano, G.; Tollari, S. Synth. Commun. 1996, 26, 495.
42. Intramolecular reactions of a nitro group and an olefin under CO pressure have already been reported by us and others to afford several types of heterocycles. However, in this case, the attack occurs at an olefin, rather than allylic carbon. For some examples see: (a) Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds, Kluwer Academic Publishers: Dordrecht, 1997; Chapter 5, and references therein, (b) Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S. J. Chem. Soc., Chem. Commun. 1986, 784. Crotti, C.; Cenini, S.; Todeschini, R.; Tollari, S. J. Chem. Soc., Faraday Trans. 1991, 87, 2811. Akazone, M.; Kondo, T.; Watanabe, Y. Chem. Lett. 1992, 769. (e) Tollari, S.; Cenini, S.; Crotti, C.; Giannella, E. J. Mol. Catal. 1994, 87, 203. (f) Tollari, S.; Cenini, S.; Ragaini, F.; Cassar, L. J. Chem. Soc., Chem. Commun. 1994, 1741. (g) Annunziata, R.; Cenini, S.; Palmisano, G.; Tollari, S. Synth. Commun. 1996, 26, 495.
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