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Volumn 33, Issue 10, 2004, Pages 1364-1365

Addition of organostannanes to isocyanate catalyzed by a rhodium complex

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ISOCYANATE; ORGANOTIN COMPOUND; PHENOL DERIVATIVE; RHODIUM COMPLEX;

EID: 11844300369     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1364     Document Type: Article
Times cited : (22)

References (24)
  • 5
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    • Addition of Grignard reagents to isocyanate: a) Y. Zhang, J. Jiang, and Y. Chen, Tetrahedron Lett., 28, 3815 (1987). b) H. M. Singleton and W. R. Edwards, Jr., J. Am. Chem. Soc., 60, 540 (1938). c) H. Gilman and M. Furry, J. Am. Chem. Soc., 50, 1214 (1928).
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3815
    • Zhang, Y.1    Jiang, J.2    Chen, Y.3
  • 6
    • 0001183250 scopus 로고
    • Addition of Grignard reagents to isocyanate: a) Y. Zhang, J. Jiang, and Y. Chen, Tetrahedron Lett., 28, 3815 (1987). b) H. M. Singleton and W. R. Edwards, Jr., J. Am. Chem. Soc., 60, 540 (1938). c) H. Gilman and M. Furry, J. Am. Chem. Soc., 50, 1214 (1928).
    • (1938) J. Am. Chem. Soc. , vol.60 , pp. 540
    • Singleton, H.M.1    Edwards Jr., W.R.2
  • 7
    • 0011445698 scopus 로고
    • Addition of Grignard reagents to isocyanate: a) Y. Zhang, J. Jiang, and Y. Chen, Tetrahedron Lett., 28, 3815 (1987). b) H. M. Singleton and W. R. Edwards, Jr., J. Am. Chem. Soc., 60, 540 (1938). c) H. Gilman and M. Furry, J. Am. Chem. Soc., 50, 1214 (1928).
    • (1928) J. Am. Chem. Soc. , vol.50 , pp. 1214
    • Gilman, H.1    Furry, M.2
  • 13
  • 14
    • 0037243669 scopus 로고    scopus 로고
    • For reviews: a) K. Fagnou and M. Lautens, Chem. Rev., 103, 169 (2003). b) A. Mori, in "Latest Frontiers of Organic Synthesis," ed. by Y. Kobayashi, Research Signpost, India (2002), pp 83-102.
    • (2003) Chem. Rev. , vol.103 , pp. 169
    • Fagnou, K.1    Lautens, M.2
  • 15
    • 2942650717 scopus 로고    scopus 로고
    • ed. by Y. Kobayashi, Research Signpost, India
    • For reviews: a) K. Fagnou and M. Lautens, Chem. Rev., 103, 169 (2003). b) A. Mori, in "Latest Frontiers of Organic Synthesis," ed. by Y. Kobayashi, Research Signpost, India (2002), pp 83-102.
    • (2002) Latest Frontiers of Organic Synthesis , pp. 83-102
    • Mori, A.1
  • 16
    • 0001363835 scopus 로고
    • Friedel-Crafts reaction of isocyanates with arylstannanes in the presence of stoichiometric Lewis acid: a) M. Arnswald and W. P. Neumann, J. Org. Chem., 58, 7022 (1993). See also: b) J. W. McFarland, and L. C. Yao, J. Org. Chem., 35, 123 (1970).
    • (1993) J. Org. Chem. , vol.58 , pp. 7022
    • Arnswald, M.1    Neumann, W.P.2
  • 17
    • 8444247498 scopus 로고
    • Friedel-Crafts reaction of isocyanates with arylstannanes in the presence of stoichiometric Lewis acid: a) M. Arnswald and W. P. Neumann, J. Org. Chem., 58, 7022 (1993). See also: b) J. W. McFarland, and L. C. Yao, J. Org. Chem., 35, 123 (1970).
    • (1970) J. Org. Chem. , vol.35 , pp. 123
    • McFarland, J.W.1    Yao, L.C.2
  • 20
    • 1042279654 scopus 로고    scopus 로고
    • Similar effect of a phenol derivative as an additive was also observed in the rhodium-catalyzed reactions: a) L. Navarre, S. Darses, and J.-P. Genet, Angew. Chem., Int. Ed., 43, 719 (2004). b) T. Fujii, T. Koike, A. Mori, and K. Osakada, Synlett, 2002, 295.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 719
    • Navarre, L.1    Darses, S.2    Genet, J.-P.3
  • 21
    • 0036172664 scopus 로고    scopus 로고
    • Similar effect of a phenol derivative as an additive was also observed in the rhodium-catalyzed reactions: a) L. Navarre, S. Darses, and J.-P. Genet, Angew. Chem., Int. Ed., 43, 719 (2004). b) T. Fujii, T. Koike, A. Mori, and K. Osakada, Synlett, 2002, 295.
    • Synlett , vol.2002 , pp. 295
    • Fujii, T.1    Koike, T.2    Mori, A.3    Osakada, K.4
  • 22
    • 11844284710 scopus 로고    scopus 로고
    • note
    • Cyclopentyl methyl ether was kindly donated by Nippon Zeon Co. Ltd.
  • 23
    • 11844249224 scopus 로고    scopus 로고
    • note
    • 2 at 120°C for 24 h to afford the conjugate addition products in 52 and 67% yields, respectively.
  • 24
    • 11844261385 scopus 로고    scopus 로고
    • note
    • The reaction of 1 with phenol at room temperature for 2 h afforded the corresponding carbamate in a quantitative yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.