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Volumn 61, Issue 5, 1996, Pages 1677-1681

Oxidative intramolecular coupling of amidocuprates as a novel route to amines and hydrazines

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EID: 0001447603     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9512315     Document Type: Article
Times cited : (45)

References (32)
  • 1
    • 0001173644 scopus 로고
    • Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 298. Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947 Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682 and references cited therein.
    • (1988) Chem. Rev. , vol.88 , pp. 298
    • Scriven, E.F.V.1    Turnbull, K.2
  • 2
    • 33845185611 scopus 로고
    • Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 298. Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947 Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682 and references cited therein.
    • (1989) Chem. Rev. , vol.89 , pp. 1947
    • Erdik, E.1    Ay, M.2
  • 3
    • 0001545275 scopus 로고
    • and references cited therein
    • Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 298. Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947 Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682 and references cited therein.
    • (1994) J. Org. Chem. , vol.59 , pp. 682
    • Mitchell, H.1    Leblanc, Y.2
  • 6
    • 0000263951 scopus 로고
    • Beak, P.; Kokko, B. J. Org. Chem. 1982, 47, 2822. Beak, P.; Basha, A.; Kokko, B.; Loo, D. K. J. Am. Chem. Soc. 1986, 108, 6016.
    • (1982) J. Org. Chem. , vol.47 , pp. 2822
    • Beak, P.1    Kokko, B.2
  • 9
    • 85033837497 scopus 로고    scopus 로고
    • note
    • The terms "higher order" (H.O.) and "lower order" (L.O.) refer to the RLi/Cu(I) ratios employed in the cuprate preparation.
  • 12
    • 0000303866 scopus 로고
    • Yamamoto, H.; Maruoka, K J. Org Chem. 1980, 45, 2739. Iwao, M.; Reed, J. N.; Snieckus, V. J. Am. Chem Soc. 1982, 104, 5531.
    • (1980) J. Org Chem. , vol.45 , pp. 2739
    • Yamamoto, H.1    Maruoka, K.2
  • 14
    • 0003467672 scopus 로고
    • Wiley: New York
    • March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992. For recent reports on substitution reactions of N-nucleophiles with aromatic substrates bearing activating groups, see also: Semmelhack, M. F.; Rhee, H. Tetrahedron Lett. 1993, 34, 1395. Hattori, T.; Sakamoto, J.; Hayashizaka N.; Miyano, S. Synthesis 1994, 199.
    • (1992) Advanced Organic Chemistry, 4th Ed.
    • March, J.1
  • 15
    • 0027535015 scopus 로고
    • March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992. For recent reports on substitution reactions of N-nucleophiles with aromatic substrates bearing activating groups, see also: Semmelhack, M. F.; Rhee, H. Tetrahedron Lett. 1993, 34, 1395. Hattori, T.; Sakamoto, J.; Hayashizaka N.; Miyano, S. Synthesis 1994, 199.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1395
    • Semmelhack, M.F.1    Rhee, H.2
  • 16
    • 0028270261 scopus 로고
    • March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992. For recent reports on substitution reactions of N-nucleophiles with aromatic substrates bearing activating groups, see also: Semmelhack, M. F.; Rhee, H. Tetrahedron Lett. 1993, 34, 1395. Hattori, T.; Sakamoto, J.; Hayashizaka N.; Miyano, S. Synthesis 1994, 199.
    • (1994) Synthesis , pp. 199
    • Hattori, T.1    Sakamoto, J.2    Hayashizaka, N.3    Miyano, S.4
  • 17
    • 0000032365 scopus 로고
    • Jansen, J. F. G. A.; Feringa, B. L. J. Org. Chem. 1990, 55, 4168. Soai, K.; Yokoyama, S.; Hayasaka, T. Ibid. 1991, 56, 4264. Brown, J. M.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 1994, 116, 866.
    • (1990) J. Org. Chem. , vol.55 , pp. 4168
    • Jansen, J.F.G.A.1    Feringa, B.L.2
  • 18
    • 33751499839 scopus 로고
    • Jansen, J. F. G. A.; Feringa, B. L. J. Org. Chem. 1990, 55, 4168. Soai, K.; Yokoyama, S.; Hayasaka, T. Ibid. 1991, 56, 4264. Brown, J. M.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 1994, 116, 866.
    • (1991) J. Org. Chem. , vol.56 , pp. 4264
    • Soai, K.1    Yokoyama, S.2    Hayasaka, T.3
  • 19
    • 0000253638 scopus 로고
    • Jansen, J. F. G. A.; Feringa, B. L. J. Org. Chem. 1990, 55, 4168. Soai, K.; Yokoyama, S.; Hayasaka, T. Ibid. 1991, 56, 4264. Brown, J. M.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 1994, 116, 866.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 866
    • Brown, J.M.1    Lloyd-Jones, G.C.2
  • 20
    • 85033837444 scopus 로고    scopus 로고
    • note
    • D +60 (c = 5, MeOH) identical with those of the starting material.
  • 22
    • 0028268144 scopus 로고
    • This synthetically unattractive reaction from which statistical ratios of three products are generated, when performed on products with mixed-ligand reagents, has been very recently reevaluated by Lipshutz through the generation of "kinetic" bis anionic cuprates. Extremely high levels of unsymmetrical ligand coupling have been achieved which allow for a novel straightforward synthesis of biaryls through inter- or intramolecular coupling: Lipshutz, B. H.; Kayser, F.; Maullin, N. Tetrahedron Lett. 1994, 35, 815. Lipshutz, B. H.; Kayser, F.; Liu, Z.-P. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 1842 and references therein.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 815
    • Lipshutz, B.H.1    Kayser, F.2    Maullin, N.3
  • 23
    • 33748222146 scopus 로고
    • and references therein
    • This synthetically unattractive reaction from which statistical ratios of three products are generated, when performed on products with mixed-ligand reagents, has been very recently reevaluated by Lipshutz through the generation of "kinetic" bis anionic cuprates. Extremely high levels of unsymmetrical ligand coupling have been achieved which allow for a novel straightforward synthesis of biaryls through inter- or intramolecular coupling: Lipshutz, B. H.; Kayser, F.; Maullin, N. Tetrahedron Lett. 1994, 35, 815. Lipshutz, B. H.; Kayser, F.; Liu, Z.-P. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 1842 and references therein.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1842
    • Lipshutz, B.H.1    Kayser, F.2    Liu, Z.-P.L.3
  • 27
    • 85033855921 scopus 로고    scopus 로고
    • note
    • • nitroxide.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.