SN2′ reaction of organozinc reagents activated by catalytic tBu-P4 base in the presence of LiCl

Chemistry - A European Journal

Volumn 15, Issue 38, 2009, Pages 9805-9809

  Kobayashi, Koji ^a   Ueno, Masahiro ^a   Naka, Hiroshi ^b   Kondo, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

Lithium; Nucleophilic substitution; Phosphazene bases; Zinc

Indexed keywords

CHEMO-AND REGIOSELECTIVITIES; HIGH YIELD; NUCLEOPHILIC SUBSTITUTIONS; ORGANOZINC REAGENTS; PHOSPHAZENE BASES; PHOSPHAZENE BASIS; SPECTROSCOPIC STUDIES; UNSATURATED ESTERS;

CHLORINE COMPOUNDS; ESTERIFICATION; LITHIUM; ORGANOMETALLICS; SPECTROSCOPIC ANALYSIS; ZINC;

ESTERS;

LITHIUM CHLORIDE; ORGANIC COMPOUND; ORGANOPHOSPHATE; TERT BUTYL PHOSPHATE; TERT-BUTYL PHOSPHATE; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; LITHIUM CHLORIDE; ORGANIC CHEMICALS; PHOSPHORIC ACID ESTERS; ZINC;

EID: 70450177797     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900556     Document Type: Article

References (26)

1. P. Knochel, P. Jones, Organozinc Reagents, Oxford University Press, Oxford, 1999.
2. P. Knöchel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188.
3. R. M. Magid, Tetrahedron 1980, 36, 1901-1930, and references therein.
4. Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2006, 128, 15604-15605.
5. a) A. O. Larsen, W. Leu, C Nieto-Oberhuber, J. E. Campbell, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 11130-11131;
6. b) J.J. Van Veldhuizen, J. E. Campbell, R. E. Giudici, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 6877-6882;
7. (c) K. E. Murphy, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4690-4691;
8. (d) K. E. Murphy, A. H. Hoveyda, Org. Lett. 2005, 7, 1255-1258;
9. e) H. Malda, A. W. van Ziji, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169-1171;
10. f) F Dübner, P. Knochel, Tetrahedron Lett. 2000, 41, 9233-9237;
11. g) F Dübner, P. Knöchel, Angew. Chem. 1999, 111, 391-393;
12. Angew. Chem. Int. Ed. 1999, 38, 379-381.
13. a) R. Schwesinger, H. Schlemper, Angew. Chem. 1987, 99, 1212-1214;
14. Angew. Chem. Int. Ed. Engl. 1987, 26, 1167-1169;
15. b) R. Schwesinger, H. Schlemper, C Hasenfratz, J. Willaredt, T. Dambacher, T. Breuer, C Ottaway, M. Fletschinger, J. Boele, H. Fritz, D. Putzas, H. W. Rotter, F. G. Bordwell, A. V. Satish, G. Z. Ji, E. M. Peters, K. Peters, H. G. von Schnering, L. Walz, Liebigs Ann. 1996, 1055-1081.
16. M. Ueno, A. E. H. Wheatley, Y. Kondo, Chem. Commun. 2006, 3549-3550.
17. A part of this work has been published as a communication: K. Kobayashi, M. Ueno, H. Naka, Y. Kondo, Chem. Commun. 2008, 3780-3782.
18. a) M. Uchiyama, M. Koike, M. Kameda, Y. Kondo, T. Sakamoto, J. Am. Chem. Soc. 1996, 118, 8733-8794;
19. b) M. Ishimori, T. Tsurua, Kogyo Kagaku Zasshi 1967, 70, 152-158.
20. a) F. F. Kneisel, M. Dochnahl, P. Knochel, Angew. Chem. 2004, 116, 1032-1036;
21. Angew. Chem. Int. Ed. 2004, 43, 1017-1021;
22. b) A. Krasovskiy, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. 2006, 116, 6186-6190;
23. Angew. Chem. Int. Ed. 2006, 45, 6040-6044;
24. (c) A. Metzger, M. A. Schade, P. Knöchel, Org. Lett. 2008, 10, 1107-1110;
25. (d) F. M. Piller, P. Appukkuttan, A. Gavryushin, M. Helm, P. Knochel, Angew. Chem. 2008, 776, 6907-6911;
26. Angew. Chem. Int. Ed. 2006, 47, 6801-6806.