A ruthenium-catalyzed three-component coupling to form E-vinyl chlorides [18]

Journal of the American Chemical Society

Volumn 121, Issue 9, 1999, Pages 1988-1989

  Trost, Barry M ^a   Pinkerton, Anthony B ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RUTHENIUM; VINYL CHLORIDE;

CATALYSIS; GAS CHROMATOGRAPHY; HYDROXYLATION; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033541098     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984264l     Document Type: Letter

References (23)

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2. For some illustrations, see: Pine, S. H. Org. React. 1994, 43, 1; Ager, D. J. Org. React. 1990, 38, 1; Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
3. For some illustrations, see: Pine, S. H. Org. React. 1994, 43, 1; Ager, D. J. Org. React. 1990, 38, 1; Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
4. Compare Mattesen, D. S. Tetrahedron 1989, 45, 1859.
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8. Trost, B. M.; Indolese, A.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.; Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888.
9. For a trans chloroalkylation of activated alkynes using palladium catalysis, see: Wang, Z.; Lu, X. Chem. Commun. 1996, 535; J. Org. Chem. 1996, 61, 2254. On the other hand, a cis chloropalladation has been claimed, see; Dietl, H.; Reinheimer, H., Moffatt, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276. Also, see: Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55. After submission of our paper, a Rh-catalyzed cis chloroalkyoxycarbonylation of alkynes has been reported, see Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
10. For a trans chloroalkylation of activated alkynes using palladium catalysis, see: Wang, Z.; Lu, X. Chem. Commun. 1996, 535; J. Org. Chem. 1996, 61, 2254. On the other hand, a cis chloropalladation has been claimed, see; Dietl, H.; Reinheimer, H., Moffatt, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276. Also, see: Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55. After submission of our paper, a Rh-catalyzed cis chloroalkyoxycarbonylation of alkynes has been reported, see Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
11. For a trans chloroalkylation of activated alkynes using palladium catalysis, see: Wang, Z.; Lu, X. Chem. Commun. 1996, 535; J. Org. Chem. 1996, 61, 2254. On the other hand, a cis chloropalladation has been claimed, see; Dietl, H.; Reinheimer, H., Moffatt, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276. Also, see: Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55. After submission of our paper, a Rh-catalyzed cis chloroalkyoxycarbonylation of alkynes has been reported, see Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
12. For a trans chloroalkylation of activated alkynes using palladium catalysis, see: Wang, Z.; Lu, X. Chem. Commun. 1996, 535; J. Org. Chem. 1996, 61, 2254. On the other hand, a cis chloropalladation has been claimed, see; Dietl, H.; Reinheimer, H., Moffatt, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276. Also, see: Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55. After submission of our paper, a Rh-catalyzed cis chloroalkyoxycarbonylation of alkynes has been reported, see Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
13. For a trans chloroalkylation of activated alkynes using palladium catalysis, see: Wang, Z.; Lu, X. Chem. Commun. 1996, 535; J. Org. Chem. 1996, 61, 2254. On the other hand, a cis chloropalladation has been claimed, see; Dietl, H.; Reinheimer, H., Moffatt, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276. Also, see: Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55. After submission of our paper, a Rh-catalyzed cis chloroalkyoxycarbonylation of alkynes has been reported, see Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
14. Naota, T.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599; Dixneuf, P. H.; Bruneau, C. In Organic Synthesis via Organometallics. OSM 5; Helmchen, G. Ed.; Vieweg Verlag: Frankfurt/am Main, 1997; pp 1-20. For a leading reference, see: Doucet, H.; Martin-Vaca, B.; Humeau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247.
15. Naota, T.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599; Dixneuf, P. H.; Bruneau, C. In Organic Synthesis via Organometallics. OSM 5; Helmchen, G. Ed.; Vieweg Verlag: Frankfurt/am Main, 1997; pp 1-20. For a leading reference, see: Doucet, H.; Martin-Vaca, B.; Humeau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247.
16. Naota, T.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599; Dixneuf, P. H.; Bruneau, C. In Organic Synthesis via Organometallics. OSM 5; Helmchen, G. Ed.; Vieweg Verlag: Frankfurt/am Main, 1997; pp 1-20. For a leading reference, see: Doucet, H.; Martin-Vaca, B.; Humeau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247.
17. Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836.
18. All new compounds have been characterized spectroscopically, and elemental composition has been established by combustion analysis or high resolution mass spectroscopy.
19. For reviews of vinyl chloride syntheses, see: Urch, C. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 2, pp 606-619; Hulce, M.; Chapdelaine, M. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelheck, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 272-278; Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B M., Fleming, I., Schreiber, S. L., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 807-809; Pattenden, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Stoddart, J. F., Eds.; Pergamon: Oxford, 1979; Vol. 1, pp 197-214. For a recent paper, see: Moughamir, K.; Mezgueldi, B.; Atmani, A.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1999, 40, 59.
20. For reviews of vinyl chloride syntheses, see: Urch, C. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 2, pp 606-619; Hulce, M.; Chapdelaine, M. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelheck, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 272-278; Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B M., Fleming, I., Schreiber, S. L., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 807-809; Pattenden, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Stoddart, J. F., Eds.; Pergamon: Oxford, 1979; Vol. 1, pp 197-214. For a recent paper, see: Moughamir, K.; Mezgueldi, B.; Atmani, A.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1999, 40, 59.
21. For reviews of vinyl chloride syntheses, see: Urch, C. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 2, pp 606-619; Hulce, M.; Chapdelaine, M. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelheck, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 272-278; Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B M., Fleming, I., Schreiber, S. L., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 807-809; Pattenden, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Stoddart, J. F., Eds.; Pergamon: Oxford, 1979; Vol. 1, pp 197-214. For a recent paper, see: Moughamir, K.; Mezgueldi, B.; Atmani, A.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1999, 40, 59.
22. For reviews of vinyl chloride syntheses, see: Urch, C. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 2, pp 606-619; Hulce, M.; Chapdelaine, M. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelheck, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 272-278; Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B M., Fleming, I., Schreiber, S. L., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 807-809; Pattenden, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Stoddart, J. F., Eds.; Pergamon: Oxford, 1979; Vol. 1, pp 197-214. For a recent paper, see: Moughamir, K.; Mezgueldi, B.; Atmani, A.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1999, 40, 59.
23. For reviews of vinyl chloride syntheses, see: Urch, C. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, 1995; Vol. 2, pp 606-619; Hulce, M.; Chapdelaine, M. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelheck, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 272-278; Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B M., Fleming, I., Schreiber, S. L., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 807-809; Pattenden, G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Stoddart, J. F., Eds.; Pergamon: Oxford, 1979; Vol. 1, pp 197-214. For a recent paper, see: Moughamir, K.; Mezgueldi, B.; Atmani, A.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1999, 40, 59.