Electrochemical regeneration of chromium(II). Alkenylation of carbonyl compounds

Synlett

Volumn , Issue 1, 1999, Pages 69-70

  Kuroboshi, Manabu ^a   Tanaka, Muneaki ^a   Kishimoto, Suguru ^a   Tanaka, Hideo ^a   Torii, Sigeru ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Alkenylation; Chromium; Electrochemistry

Indexed keywords

CARBONYL DERIVATIVE; CHROMIUM;

ANALYTIC METHOD; ARTICLE; COMPLEX FORMATION; DERIVATIZATION; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; ELECTROCHEMISTRY; RECYCLING; REGENERATION;

EID: 0032915618     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2555     Document Type: Article

References (20)

1. Comprehensive Organometallic Chemistry II. Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: Oxford 1995.
2. Torii, S. Interface 1997, 46. For reviews: Torii, S. in New Challenges in Organic Electrochemistry Osa, T. Ed.; Gordon and Breach Science Publishers: 1998. Bersier, P. M.; Carlosson, L.; Bersier, J. in Top. Curr. Chem. Steckhan, E. Ed.; Springer-Verlag: Berlin, 1994, 110, p 113. Torii, S. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1024. Simonet, J. in Organic Electrochemistry, 3rd. Ed.; Lund, H.; Baizer, M. M. Eds.; Marcel Dekker Inc.: NY, 1991, p 1217. Efimov, O. L.; Strelets, V. V. Coord. Chem. Rev. 1991, 99, 15. Torii, S. Synthesis 1986, 873.
3. Torii, S. Interface 1997, 46. For reviews: Torii, S. in New Challenges in Organic Electrochemistry Osa, T. Ed.; Gordon and Breach Science Publishers: 1998. Bersier, P. M.; Carlosson, L.; Bersier, J. in Top. Curr. Chem. Steckhan, E. Ed.; Springer-Verlag: Berlin, 1994, 110, p 113. Torii, S. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1024. Simonet, J. in Organic Electrochemistry, 3rd. Ed.; Lund, H.; Baizer, M. M. Eds.; Marcel Dekker Inc.: NY, 1991, p 1217. Efimov, O. L.; Strelets, V. V. Coord. Chem. Rev. 1991, 99, 15. Torii, S. Synthesis 1986, 873.
4. Torii, S. Interface 1997, 46. For reviews: Torii, S. in New Challenges in Organic Electrochemistry Osa, T. Ed.; Gordon and Breach Science Publishers: 1998. Bersier, P. M.; Carlosson, L.; Bersier, J. in Top. Curr. Chem. Steckhan, E. Ed.; Springer-Verlag: Berlin, 1994, 110, p 113. Torii, S. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1024. Simonet, J. in Organic Electrochemistry, 3rd. Ed.; Lund, H.; Baizer, M. M. Eds.; Marcel Dekker Inc.: NY, 1991, p 1217. Efimov, O. L.; Strelets, V. V. Coord. Chem. Rev. 1991, 99, 15. Torii, S. Synthesis 1986, 873.
5. Torii, S. Interface 1997, 46. For reviews: Torii, S. in New Challenges in Organic Electrochemistry Osa, T. Ed.; Gordon and Breach Science Publishers: 1998. Bersier, P. M.; Carlosson, L.; Bersier, J. in Top. Curr. Chem. Steckhan, E. Ed.; Springer-Verlag: Berlin, 1994, 110, p 113. Torii, S. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1024. Simonet, J. in Organic Electrochemistry, 3rd. Ed.; Lund, H.; Baizer, M. M. Eds.; Marcel Dekker Inc.: NY, 1991, p 1217. Efimov, O. L.; Strelets, V. V. Coord. Chem. Rev. 1991, 99, 15. Torii, S. Synthesis 1986, 873.
6. Torii, S. Interface 1997, 46. For reviews: Torii, S. in New Challenges in Organic Electrochemistry Osa, T. Ed.; Gordon and Breach Science Publishers: 1998. Bersier, P. M.; Carlosson, L.; Bersier, J. in Top. Curr. Chem. Steckhan, E. Ed.; Springer-Verlag: Berlin, 1994, 110, p 113. Torii, S. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1024. Simonet, J. in Organic Electrochemistry, 3rd. Ed.; Lund, H.; Baizer, M. M. Eds.; Marcel Dekker Inc.: NY, 1991, p 1217. Efimov, O. L.; Strelets, V. V. Coord. Chem. Rev. 1991, 99, 15. Torii, S. Synthesis 1986, 873.
7. Torii, S. Interface 1997, 46. For reviews: Torii, S. in New Challenges in Organic Electrochemistry Osa, T. Ed.; Gordon and Breach Science Publishers: 1998. Bersier, P. M.; Carlosson, L.; Bersier, J. in Top. Curr. Chem. Steckhan, E. Ed.; Springer-Verlag: Berlin, 1994, 110, p 113. Torii, S. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1024. Simonet, J. in Organic Electrochemistry, 3rd. Ed.; Lund, H.; Baizer, M. M. Eds.; Marcel Dekker Inc.: NY, 1991, p 1217. Efimov, O. L.; Strelets, V. V. Coord. Chem. Rev. 1991, 99, 15. Torii, S. Synthesis 1986, 873.
8. Torii, S. Interface 1997, 46. For reviews: Torii, S. in New Challenges in Organic Electrochemistry Osa, T. Ed.; Gordon and Breach Science Publishers: 1998. Bersier, P. M.; Carlosson, L.; Bersier, J. in Top. Curr. Chem. Steckhan, E. Ed.; Springer-Verlag: Berlin, 1994, 110, p 113. Torii, S. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1024. Simonet, J. in Organic Electrochemistry, 3rd. Ed.; Lund, H.; Baizer, M. M. Eds.; Marcel Dekker Inc.: NY, 1991, p 1217. Efimov, O. L.; Strelets, V. V. Coord. Chem. Rev. 1991, 99, 15. Torii, S. Synthesis 1986, 873.
9. Takai, K.; Kimura, K.; Kuroda,T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. Nicholas, A. S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Schreiber, S. L. Eds.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 1.6.
10. Takai, K.; Kimura, K.; Kuroda,T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. Nicholas, A. S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Schreiber, S. L. Eds.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 1.6.
11. Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644. Dyer, U. C.; Kishi, Y. J. Org. Chem. 1988, 53, 3383.
12. Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644. Dyer, U. C.; Kishi, Y. J. Org. Chem. 1988, 53, 3383.
13. During our course of study, preliminary results of electrochemical Pd/Cr mediated vinylation in a divided cell was reported. Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307. Fürstner used Mn as a reductant of Cr(III), wherein a large amount of Mn salts were generated as a pollutive waste. Furstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349.
14. During our course of study, preliminary results of electrochemical Pd/Cr mediated vinylation in a divided cell was reported. Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307. Fürstner used Mn as a reductant of Cr(III), wherein a large amount of Mn salts were generated as a pollutive waste. Furstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349.
15. Steckhan reported Cr-promoted electrochemical homocoupling of benzyl and allyl halide. Wellmann, J.; Steckhan, E. Synthesis 1978, 901. Cr-mediated electrochemical pinacol coupling was reported by Utley. Sopher, D. W.; Utley, J. H. P. J. Chem. Soc., Perkin Trans. II 1984, 1361. J. Chem. Soc., Chem. Commun. 1979, 1087.
16. Steckhan reported Cr-promoted electrochemical homocoupling of benzyl and allyl halide. Wellmann, J.; Steckhan, E. Synthesis 1978, 901. Cr-mediated electrochemical pinacol coupling was reported by Utley. Sopher, D. W.; Utley, J. H. P. J. Chem. Soc., Perkin Trans. II 1984, 1361. J. Chem. Soc., Chem. Commun. 1979, 1087.
17. Steckhan reported Cr-promoted electrochemical homocoupling of benzyl and allyl halide. Wellmann, J.; Steckhan, E. Synthesis 1978, 901. Cr-mediated electrochemical pinacol coupling was reported by Utley. Sopher, D. W.; Utley, J. H. P. J. Chem. Soc., Perkin Trans. II 1984, 1361. J. Chem. Soc., Chem. Commun. 1979, 1087.
18. A part of the silyl ether was hydrolyzed to afford the corresponding alcohol during purification by silica-gel column chromatography.
19. 3 did not dissolve in DMF.
20. This isomerization might be caused by Lewis acidic aluminium salts such as AlBr, generated during electrolysis.