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Volumn 71, Issue 8, 2006, Pages 3184-3191

Tetrasubstituted olefin synthesis via Pd-catalyzed addition of arylboronic acids to internal alkynes using O2 as an oxidant

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; MOLECULAR DYNAMICS; OLEFINS; OXIDATION; SYNTHESIS (CHEMICAL);

EID: 33645789010     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060104d     Document Type: Article
Times cited : (71)

References (51)
  • 6
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    • and references therein
    • (f) Zhou, C.; Larock, R. C. J. Org. Chem. 2005, 70, 3765 and references therein.
    • (2005) J. Org. Chem. , vol.70 , pp. 3765
    • Zhou, C.1    Larock, R.C.2
  • 8
    • 0026418434 scopus 로고
    • (a) Trost, B. Science 1991, 234, 1471.
    • (1991) Science , vol.234 , pp. 1471
    • Trost, B.1
  • 24
    • 18044402758 scopus 로고    scopus 로고
    • For an example involving the formation of a highly substituted cyclopentadiene, see: (c) Du, X.; Suguro, M.; Hirabayashi, K.; Mori A. Org. Lett. 2001, 3, 3313.
    • (2001) Org. Lett. , vol.3 , pp. 3313
    • Du, X.1    Suguro, M.2    Hirabayashi, K.3    Mori, A.4
  • 26
    • 24944468108 scopus 로고    scopus 로고
    • (a) Stahl, S. S. Science 2005, 309, 1824.
    • (2005) Science , vol.309 , pp. 1824
    • Stahl, S.S.1
  • 27
    • 4143153074 scopus 로고    scopus 로고
    • and references therein
    • (b) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400 and references therein,
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3400
    • Stahl, S.S.1
  • 37
    • 0000700023 scopus 로고
    • For the homocoupling of boronic acids or esters in the presence of a base, see: (a) Miyaura, N.; Suzuki, A. Main Group Met. Chem. 1987, 10, 295.
    • (1987) Main Group Met. Chem. , vol.10 , pp. 295
    • Miyaura, N.1    Suzuki, A.2
  • 47
    • 33645764549 scopus 로고    scopus 로고
    • note
    • ( 13) Entry 7 was chosen as the "optimal" conditions for exploring the scope of this chemistry because of the convenience of product purification. However, the stoichiometry is not necessarily the best stoichiometry from an atom-economical view. Considering the availability of the starting alkynes and boronic acids, one can certainly run the reaction using other stoichiometries for better use of all reagents.
  • 48
    • 33645759368 scopus 로고    scopus 로고
    • note
    • See Supporting Information in ret 10 for detailed information.
  • 49
    • 0141714650 scopus 로고    scopus 로고
    • The cis addition of arylpalladium intermediates to internal alkynes is generally observed in carbopalladation processes. For representative reviews of carbopalladation, see ref 2b,c and: (a) Larock, R. C. Pure Appl. Chem. 1999, 71, 1453.
    • (1999) Pure Appl. Chem. , vol.71 , pp. 1453
    • Larock, R.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.