A bimetallic ruthenium ethylene complex as a catalyst precursor for the Kharasch reaction

Organometallics

Volumn 24, Issue 7, 2005, Pages 1404-1406

  Quebatte, Laurent ^a   Solari, Euro ^a   Scopelliti, Rosario ^a   Severin, Kay ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSTS; OLEFINS; ORGANOMETALLICS; SOLUBILITY; SOLVENTS;

ATOM TRANSFER RADICAL REACTIONS; KHARASCH REACTION; METHYLENE CHLORIDE; PRECURSORS;

RUTHENIUM COMPOUNDS;

EID: 16244367170     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050027x     Document Type: Article

References (32)

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8. For some selected examples see: (a) Quebatte, L.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2004, 43, 1520. (b) Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391. (c) Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Viñas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421. (d) Tutusaus, O.; Viñas, C.; Núñez, R.; Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830. (e) Opstal, T.; Verpoort, F. New J. Chem. 2003, 27, 257. (f) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11. (g) Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Eur. J. Org. Chem. 2001, 2689. (h) Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
9. For some selected examples see: (a) Quebatte, L.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2004, 43, 1520. (b) Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391. (c) Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Viñas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421. (d) Tutusaus, O.; Viñas, C.; Núñez, R.; Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830. (e) Opstal, T.; Verpoort, F. New J. Chem. 2003, 27, 257. (f) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11. (g) Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Eur. J. Org. Chem. 2001, 2689. (h) Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
10. For some selected examples see: (a) Quebatte, L.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2004, 43, 1520. (b) Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391. (c) Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Viñas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421. (d) Tutusaus, O.; Viñas, C.; Núñez, R.; Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830. (e) Opstal, T.; Verpoort, F. New J. Chem. 2003, 27, 257. (f) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11. (g) Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Eur. J. Org. Chem. 2001, 2689. (h) Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
11. For some selected examples see: (a) Quebatte, L.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2004, 43, 1520. (b) Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391. (c) Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Viñas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421. (d) Tutusaus, O.; Viñas, C.; Núñez, R.; Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830. (e) Opstal, T.; Verpoort, F. New J. Chem. 2003, 27, 257. (f) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11. (g) Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Eur. J. Org. Chem. 2001, 2689. (h) Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
12. For some selected examples see: (a) Quebatte, L.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2004, 43, 1520. (b) Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391. (c) Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Viñas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421. (d) Tutusaus, O.; Viñas, C.; Núñez, R.; Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830. (e) Opstal, T.; Verpoort, F. New J. Chem. 2003, 27, 257. (f) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11. (g) Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Eur. J. Org. Chem. 2001, 2689. (h) Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
13. For some selected examples see: (a) Quebatte, L.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2004, 43, 1520. (b) Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391. (c) Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Viñas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421. (d) Tutusaus, O.; Viñas, C.; Núñez, R.; Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830. (e) Opstal, T.; Verpoort, F. New J. Chem. 2003, 27, 257. (f) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11. (g) Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Eur. J. Org. Chem. 2001, 2689. (h) Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
14. For some selected examples see: (a) Quebatte, L.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2004, 43, 1520. (b) Lee, B. T.; Schrader, T. O.; Martín-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391. (c) Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Viñas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421. (d) Tutusaus, O.; Viñas, C.; Núñez, R.; Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830. (e) Opstal, T.; Verpoort, F. New J. Chem. 2003, 27, 257. (f) De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11. (g) Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Eur. J. Org. Chem. 2001, 2689. (h) Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
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16. 4): δ (ppm) 44.37 (s). Anal. Calcd for S-(toluene): C, 50.57; H, 6.77. Found: C, 50.25; H, 6.72.
17. 2(all data) = 0.0613.
18. For some recent reports about mixed, halogeno-bridged complexes see: (a) Gauthier, S.; Scopelliti, R.; Severin, K. Organometallics 2004, 23, 3769. (b) Gauthier, S.; Quebatte, L.; Scopelliti, R.; Severin, K. Chem. Eur. J. 2004, 10, 2811. (c) Gauthier, S.; Quebatte, L.; Scopelliti, R.; Severin, K. Inorg. Chem. Commun. 2004, 7, 708. (d) Severin, K. Chem. Eur. J. 2002, 8, 1514 and references cited therein.
19. For some recent reports about mixed, halogeno-bridged complexes see: (a) Gauthier, S.; Scopelliti, R.; Severin, K. Organometallics 2004, 23, 3769. (b) Gauthier, S.; Quebatte, L.; Scopelliti, R.; Severin, K. Chem. Eur. J. 2004, 10, 2811. (c) Gauthier, S.; Quebatte, L.; Scopelliti, R.; Severin, K. Inorg. Chem. Commun. 2004, 7, 708. (d) Severin, K. Chem. Eur. J. 2002, 8, 1514 and references cited therein.
20. For some recent reports about mixed, halogeno-bridged complexes see: (a) Gauthier, S.; Scopelliti, R.; Severin, K. Organometallics 2004, 23, 3769. (b) Gauthier, S.; Quebatte, L.; Scopelliti, R.; Severin, K. Chem. Eur. J. 2004, 10, 2811. (c) Gauthier, S.; Quebatte, L.; Scopelliti, R.; Severin, K. Inorg. Chem. Commun. 2004, 7, 708. (d) Severin, K. Chem. Eur. J. 2002, 8, 1514 and references cited therein.
21. For some recent reports about mixed, halogeno-bridged complexes see: (a) Gauthier, S.; Scopelliti, R.; Severin, K. Organometallics 2004, 23, 3769. (b) Gauthier, S.; Quebatte, L.; Scopelliti, R.; Severin, K. Chem. Eur. J. 2004, 10, 2811. (c) Gauthier, S.; Quebatte, L.; Scopelliti, R.; Severin, K. Inorg. Chem. Commun. 2004, 7, 708. (d) Severin, K. Chem. Eur. J. 2002, 8, 1514 and references cited therein.
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27. 2O.
28. Lower values for the yield compared to the conversion are frequently found for Kharasch reactions. This is mainly due to polymerization reactions which compete with the addition reaction.
29. 2(all data) = 0.0758.
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