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Volumn 346, Issue 13-15, 2004, Pages 1765-1772

Rhodium-catalyzed coupling reaction of aroyl chlorides with alkenes

Author keywords

C C coupling; Cyclization; Heck reaction; Homogeneous catalysis; Rhodium

Indexed keywords

ALKENE DERIVATIVE; CHLORIDE; ETHYLENE; RHODIUM;

EID: 12344295406     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404145     Document Type: Article
Times cited : (62)

References (44)
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    • The coupling with alkenes was successful when norbornenes were used in the presence of a disilane, giving aroylarylation products: K. Kokubo, K. Matsumasa, M. Miura, M. Nomura, J. Organomet. Chem. 1998, 560, 217.
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    • however, we were unable to reproduce the reported reaction
    • For an example of the Mizoroki-Heck reaction in which a Wilkinson complex was used as catalyst, see: S. Iyer, J. Organomet. Chem. 1995, 490, C27; however, we were unable to reproduce the reported reaction.
    • (1995) J. Organomet. Chem. , vol.490
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    • Preliminary communication: T. Sugihara, T. Satoh, M. Miura, M. Nomura, Angew. Chem. 2003, 115, 4820; Angew. Chem. Int. Ed. 2003, 42, 4672.
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    • M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries, Angew. Chem. 1998, 110, 688; Angew. Chem. Int. Ed. 1998, 37, 662.
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    • b) L. J. Gooßen, J. Paetzold, Angew. Chem. 2004, 116, 1115; Angew. Chem. Int. Ed. 2004, 43, 1095.
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    • We also reported that the iridium-catalyzed coupling of aroyl chlorides with internal alkynes can proceed under base-free conditions: T. Yasukawa, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2002, 124, 12680.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12680
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    • note
    • The reaction of 1a with N-tert-butylacrylamide, however, was not successful; an undesired acyl exchange took place to give N-tert-butylbenzamide as the major product.
  • 30
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    • note
    • In the reaction with 5, only a trace amount of α-phenylated product was detected by GC-MS.
  • 31
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    • For an example of a Mizoroki-Heck type reaction involving an arylrhodium(I) intermediate, see: a) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169; b) A. Mori, Y. Danda, T. Fujii, K. Hirabayashi, K. Osakada, J. Am. Chem. Soc. 2001, 123, 10774.
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    • Fagnou, K.1    Lautens, M.2
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    • For an example of a Mizoroki-Heck type reaction involving an arylrhodium(I) intermediate, see: a) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169; b) A. Mori, Y. Danda, T. Fujii, K. Hirabayashi, K. Osakada, J. Am. Chem. Soc. 2001, 123, 10774.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10774
    • Mori, A.1    Danda, Y.2    Fujii, T.3    Hirabayashi, K.4    Osakada, K.5
  • 44
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    • Adv. Synth. Catal. 2004, 346, 1773-1781
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1773-1781


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.