메뉴 건너뛰기




Volumn 130, Issue 49, 2008, Pages 16474-16475

Indole synthesis via rhodium catalyzed oxidative coupling of acetanilides and internal alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE; ALKYNE; INDOLE; RHODIUM;

EID: 57549086217     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806955s     Document Type: Article
Times cited : (664)

References (40)
  • 1
    • 57549112617 scopus 로고    scopus 로고
    • A Beilstein search yielded >45 000 results for indoles with biological activity.
    • A Beilstein search yielded >45 000 results for indoles with biological activity.
  • 11
    • 2942609168 scopus 로고    scopus 로고
    • For a review, see: a
    • For a review, see: (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
    • (2004) Chem. Rev , vol.104 , pp. 2285
    • Zeni, G.1    Larock, R.C.2
  • 12
    • 0001304357 scopus 로고
    • For selected individual accounts, see: b
    • For selected individual accounts, see: (b) Tida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938.
    • (1980) J. Org. Chem , vol.45 , pp. 2938
    • Tida, H.1    Yuasa, Y.2    Kibayashi, C.3
  • 24
    • 57549102160 scopus 로고    scopus 로고
    • ortho-Iodoaniline is $1070/mol, whereas aniline is $12/mol.
    • ortho-Iodoaniline is $1070/mol, whereas aniline is $12/mol.
  • 30
    • 38849126856 scopus 로고    scopus 로고
    • For recent examples in oxidative biaryl formation, see: e
    • For recent examples in oxidative biaryl formation, see: (e) Li, B.-L.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 1115
    • Li, B.-L.1    Tian, S.-L.2    Fang, Z.3    Shi, Z.-J.4
  • 32
    • 0000155817 scopus 로고    scopus 로고
    • Only unreacted acetanilide (1a) and trace amounts of a multiple alkyne insertion product previously observed by Heck appeared in the GCMS trace. Wu, G.; Rheingold, A. L.; Heck, R. F. Organometallics 1986, 5, 1922.
    • Only unreacted acetanilide (1a) and trace amounts of a multiple alkyne insertion product previously observed by Heck appeared in the GCMS trace. Wu, G.; Rheingold, A. L.; Heck, R. F. Organometallics 1986, 5, 1922.
  • 37
    • 0042626231 scopus 로고    scopus 로고
    • For the use of this complex in the cleavage of other stong bonds, see
    • For the use of this complex in the cleavage of other stong bonds, see: Taw, F. L.; Mueller, A. H.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 9808.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 9808
    • Taw, F.L.1    Mueller, A.H.2    Bergman, R.G.3    Brookhart, M.4
  • 38
    • 0001538186 scopus 로고    scopus 로고
    • A similar effect has been observed in rhodium catalyzed carbonylation reactions. See
    • A similar effect has been observed in rhodium catalyzed carbonylation reactions. See: Grushin, V. V.; Marshall, W. J.; Thorn, D. L. Adv. Synth. Catal. 2001, 343, 161.
    • (2001) Adv. Synth. Catal , vol.343 , pp. 161
    • Grushin, V.V.1    Marshall, W.J.2    Thorn, D.L.3
  • 39
    • 57549118992 scopus 로고    scopus 로고
    • In the reaction yielding 3a the regioselectivity is >40:1 by GCMS
    • In the reaction yielding 3a the regioselectivity is >40:1 by GCMS.
  • 40
    • 57549113361 scopus 로고    scopus 로고
    • All yields for deacetylation were equal to or greater than 90%, and reaction times were between 15 min to 1 h. Please see Supporting Information for specific conditions and representative examples.
    • All yields for deacetylation were equal to or greater than 90%, and reaction times were between 15 min to 1 h. Please see Supporting Information for specific conditions and representative examples.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.