Reactivity and selectivity of ortho-metalated rhodium(II) complexes in C-H insertion reactions of α-diazo compounds

Organometallics

Volumn 17, Issue 16, 1998, Pages 3442-3447

  Estevan, Francisco ^a   Lahuerta, Pascual ^a   Pérez Prieto, Julia ^a   Pereira, Inés ^a   Stiriba, Salah Eddine ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000854711     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om971070q     Document Type: Article

References (31)

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2. For reviews: (a) Padwa, A.; Austin, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (c) McKervey, M. A.; Doyle, M. P. J. Chem. Soc., Chem. Commun. 1997, 983-1072. (d) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis; Moser, W. R., Slocum, D. W., Eds.; ACS Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (e) Taber, D. F. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, p 1045. (f) Taber, D. F. Methods of Organic Chemistry; HoubenWeyl; Helmchen, G., Hoffman, W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, Germany, 1995; p 1127. (g) Doyle, M. P. Chem. Rev. 1986, 86. (h) Wulff, W. D. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5.
3. For reviews: (a) Padwa, A.; Austin, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (c) McKervey, M. A.; Doyle, M. P. J. Chem. Soc., Chem. Commun. 1997, 983-1072. (d) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis; Moser, W. R., Slocum, D. W., Eds.; ACS Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (e) Taber, D. F. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, p 1045. (f) Taber, D. F. Methods of Organic Chemistry; HoubenWeyl; Helmchen, G., Hoffman, W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, Germany, 1995; p 1127. (g) Doyle, M. P. Chem. Rev. 1986, 86. (h) Wulff, W. D. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5.
4. For reviews: (a) Padwa, A.; Austin, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (c) McKervey, M. A.; Doyle, M. P. J. Chem. Soc., Chem. Commun. 1997, 983-1072. (d) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis; Moser, W. R., Slocum, D. W., Eds.; ACS Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (e) Taber, D. F. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, p 1045. (f) Taber, D. F. Methods of Organic Chemistry; HoubenWeyl; Helmchen, G., Hoffman, W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, Germany, 1995; p 1127. (g) Doyle, M. P. Chem. Rev. 1986, 86. (h) Wulff, W. D. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5.
5. For reviews: (a) Padwa, A.; Austin, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (c) McKervey, M. A.; Doyle, M. P. J. Chem. Soc., Chem. Commun. 1997, 983-1072. (d) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis; Moser, W. R., Slocum, D. W., Eds.; ACS Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (e) Taber, D. F. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, p 1045. (f) Taber, D. F. Methods of Organic Chemistry; HoubenWeyl; Helmchen, G., Hoffman, W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, Germany, 1995; p 1127. (g) Doyle, M. P. Chem. Rev. 1986, 86. (h) Wulff, W. D. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5.
6. For reviews: (a) Padwa, A.; Austin, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (c) McKervey, M. A.; Doyle, M. P. J. Chem. Soc., Chem. Commun. 1997, 983-1072. (d) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis; Moser, W. R., Slocum, D. W., Eds.; ACS Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (e) Taber, D. F. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, p 1045. (f) Taber, D. F. Methods of Organic Chemistry; HoubenWeyl; Helmchen, G., Hoffman, W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, Germany, 1995; p 1127. (g) Doyle, M. P. Chem. Rev. 1986, 86. (h) Wulff, W. D. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5.
7. For reviews: (a) Padwa, A.; Austin, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (c) McKervey, M. A.; Doyle, M. P. J. Chem. Soc., Chem. Commun. 1997, 983-1072. (d) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis; Moser, W. R., Slocum, D. W., Eds.; ACS Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (e) Taber, D. F. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, p 1045. (f) Taber, D. F. Methods of Organic Chemistry; HoubenWeyl; Helmchen, G., Hoffman, W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, Germany, 1995; p 1127. (g) Doyle, M. P. Chem. Rev. 1986, 86. (h) Wulff, W. D. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5.
8. For reviews: (a) Padwa, A.; Austin, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091. (c) McKervey, M. A.; Doyle, M. P. J. Chem. Soc., Chem. Commun. 1997, 983-1072. (d) Doyle, M. P. In Homogeneous Transition Metal Catalysts in Organic Synthesis; Moser, W. R., Slocum, D. W., Eds.; ACS Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; Chapter 30. (e) Taber, D. F. Comprehensive Organic Synthesis; Pergamon Press: Oxford, U.K., 1991; Vol. 3, p 1045. (f) Taber, D. F. Methods of Organic Chemistry; HoubenWeyl; Helmchen, G., Hoffman, W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, Germany, 1995; p 1127. (g) Doyle, M. P. Chem. Rev. 1986, 86. (h) Wulff, W. D. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5.
9. For relevant examples in Rh(II)-mediated C-H insertion, see: (a) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; Van Basten, A.; Muller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296. (c) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Person, M. M. J. Am. Chem. Soc. 1993, 115, 958. (d) Taber, D. F.; Amedio, J. C., Jr.; Raman, K. J. Org. Chem. 1988, 53, 2984.
10. For relevant examples in Rh(II)-mediated C-H insertion, see: (a) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; Van Basten, A.; Muller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296. (c) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Person, M. M. J. Am. Chem. Soc. 1993, 115, 958. (d) Taber, D. F.; Amedio, J. C., Jr.; Raman, K. J. Org. Chem. 1988, 53, 2984.
11. For relevant examples in Rh(II)-mediated C-H insertion, see: (a) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; Van Basten, A.; Muller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296. (c) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Person, M. M. J. Am. Chem. Soc. 1993, 115, 958. (d) Taber, D. F.; Amedio, J. C., Jr.; Raman, K. J. Org. Chem. 1988, 53, 2984.
12. For relevant examples in Rh(II)-mediated C-H insertion, see: (a) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Canas, F.; Pierson, D. A.; Van Basten, A.; Muller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296. (c) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Person, M. M. J. Am. Chem. Soc. 1993, 115, 958. (d) Taber, D. F.; Amedio, J. C., Jr.; Raman, K. J. Org. Chem. 1988, 53, 2984.
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