TMP-zincate as highly chemoselective base for directed ortho metalation [6]

Journal of the American Chemical Society

Volumn 121, Issue 14, 1999, Pages 3539-3540

  Kondo, Yoshinori ^a   Shilai, Manabu ^a   Uchiyama, Masanobu ^a   Sakamoto, Takao ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM DI(TERT BUTYLTETRAMETHYLPIPERIDINOZINCATE); POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; SYNTHESIS;

EID: 0033553109     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984263t     Document Type: Letter

References (45)

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35. Direct α-metalation of π-deficient aza-aromatics has been carried out by the activation of substrates using in situ complexation. (a) Taylor, S. L.; Lee, D. Y.; Martin, J. C. J. Org. Chem. 1983, 48, 4158-4159. (b) Kessar, S. V.; Singh, P.; Singh, K. N.; Dutt, M. J. Chem. Soc., Chem. Commun. 1991, 570-571. (c) Kessar, S. V.; Singh, P. Chem. Rev. 1997, 97, 721-737. (d) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. (e) Vedejs, E.; Monahan, S. J. Org. Chem. 1996, 61, 5192-5193.
36. Direct α-metalation of π-deficient aza-aromatics has been carried out by the activation of substrates using in situ complexation. (a) Taylor, S. L.; Lee, D. Y.; Martin, J. C. J. Org. Chem. 1983, 48, 4158-4159. (b) Kessar, S. V.; Singh, P.; Singh, K. N.; Dutt, M. J. Chem. Soc., Chem. Commun. 1991, 570-571. (c) Kessar, S. V.; Singh, P. Chem. Rev. 1997, 97, 721-737. (d) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. (e) Vedejs, E.; Monahan, S. J. Org. Chem. 1996, 61, 5192-5193.
37. Direct α-metalation of π-deficient aza-aromatics has been carried out by the activation of substrates using in situ complexation. (a) Taylor, S. L.; Lee, D. Y.; Martin, J. C. J. Org. Chem. 1983, 48, 4158-4159. (b) Kessar, S. V.; Singh, P.; Singh, K. N.; Dutt, M. J. Chem. Soc., Chem. Commun. 1991, 570-571. (c) Kessar, S. V.; Singh, P. Chem. Rev. 1997, 97, 721-737. (d) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809-1810. (e) Vedejs, E.; Monahan, S. J. Org. Chem. 1996, 61, 5192-5193.
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39. -1.
40. 13C NMR spectra.
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42. For recent studies on the mechanism of ortho lithiation, see: (a) Rennels, R. A.; Maliakal, A. J.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 421-422. (b) Saa, J. M.; Martorell, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194-5195. (c) Saa, J. M.; Deya, P. M.; Guillem, A.; Suner, A.; Frontera, A. J. Am. Chem. Soc. 1992, 114, 9093-9100. (d) Bauer, W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1989, 111, 7191-7198.
43. For recent studies on the mechanism of ortho lithiation, see: (a) Rennels, R. A.; Maliakal, A. J.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 421-422. (b) Saa, J. M.; Martorell, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194-5195. (c) Saa, J. M.; Deya, P. M.; Guillem, A.; Suner, A.; Frontera, A. J. Am. Chem. Soc. 1992, 114, 9093-9100. (d) Bauer, W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1989, 111, 7191-7198.
44. For recent studies on the mechanism of ortho lithiation, see: (a) Rennels, R. A.; Maliakal, A. J.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 421-422. (b) Saa, J. M.; Martorell, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194-5195. (c) Saa, J. M.; Deya, P. M.; Guillem, A.; Suner, A.; Frontera, A. J. Am. Chem. Soc. 1992, 114, 9093-9100. (d) Bauer, W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1989, 111, 7191-7198.
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