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Volumn 74, Issue 15, 2009, Pages 5471-5475

Platinum and ruthenium chloride-catalyzed cycloisomerization of 1-alkyl-2-ethynylbenzenes: Interception of π-activated alkynes with a benzylic C-H bond

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED ALKYNES; AIR-STABLE; AMBIENT TEMPERATURES; BENZYLIC; C-H BOND; CHEMICAL EQUATIONS; CYCLOISOMERIZATION; H-BONDS; KINETIC ISOTOPES; MECHANISTIC STUDIES; RUTHENIUM CHLORIDES; SUBSTITUENT EFFECT;

EID: 68049099258     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901045g     Document Type: Article
Times cited : (112)

References (52)
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    • Selected reviews on catalytic hydroarylation of alkynes: (a) Nevado, C.; Echavarren, A. M. Synthesis 2005, 167.
  • 17
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    • Interception of metal carbenoid species via double cyclopropanation: (a) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
    • Interception of metal carbenoid species via double cyclopropanation: (a) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
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    • (e) Seregin, I. V.; W., S. A.; Gevorgyan, V. Tetrahedron 2008, 64, 6876.
  • 31
    • 33745777313 scopus 로고    scopus 로고
    • For recent reviews on catalytic reactions involving vinylidene intermediates, see: a
    • For recent reviews on catalytic reactions involving vinylidene intermediates, see: (a) Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 2176
    • Bruneau, C.1    Dixneuf, P.H.2
  • 39
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    • With a similar substrate, 38% yield after 100 h of stirring at 105°C was obtained with a Ru catalyst. See ref 6b
    • With a similar substrate, 38% yield after 100 h of stirring at 105°C was obtained with a Ru catalyst. See ref 6b.
  • 40
    • 68049090380 scopus 로고    scopus 로고
    • The reaction did not proceed under conditions similar to that reported by Yamamoto 10 mol, PtBr2 in CH3CN at 60°C, See ref 4d
    • 3CN at 60°C). See ref 4d.
  • 41
    • 68049083126 scopus 로고    scopus 로고
    • 3, afforded no desired product.
    • 3, afforded no desired product.
  • 42
    • 68049093524 scopus 로고    scopus 로고
    • With a TpRu catalyst, isomerization to silyl enol ether occurred predominantly. See ref 6b
    • With a TpRu catalyst, isomerization to silyl enol ether occurred predominantly. See ref 6b.
  • 51
    • 59949103940 scopus 로고    scopus 로고
    • Chirality transfer is accomplished in some gold-catalyzed cycloisomerizations, in which carbocationic intermediates are involved. Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2008, 10, 2649. See also ref 12.
    • Chirality transfer is accomplished in some gold-catalyzed cycloisomerizations, in which carbocationic intermediates are involved. Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2008, 10, 2649. See also ref 12.
  • 52
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    • Onthe submission of this manuscript, a similar transformation using internal alkynes has been reported: Yang, S.; Li, Z.; Jian, X.; He, C. Angew. Chem., Int. Ed. 2009, 48, 3999.
    • Onthe submission of this manuscript, a similar transformation using internal alkynes has been reported: Yang, S.; Li, Z.; Jian, X.; He, C. Angew. Chem., Int. Ed. 2009, 48, 3999.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.