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Volumn 131, Issue 50, 2009, Pages 18022-18023

Catalyzed catalysis using carbophilic Lewis acidic gold and Lewis basic palladium: Synthesis of substituted butenolides and isocoumarins

Author keywords

[No Author keywords available]

Indexed keywords

BUTENOLIDES; CATALYTIC REACTIVITY; CROSS-COUPLINGS; GOLD COMPLEXES; ISOCOUMARINS; LEWIS ACIDIC; NEW STRATEGY;

EID: 72449169570     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9068497     Document Type: Article
Times cited : (209)

References (30)
  • 4
    • 0032483548 scopus 로고    scopus 로고
    • For a Ag/Pd cross-coupling reaction limited to carboxylic acids, see
    • For a Ag/Pd cross-coupling reaction limited to carboxylic acids, see: Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387.
    • (1998) J. Org. Chem. , vol.63 , pp. 6387
    • Ma, S.1    Shi, Z.2
  • 5
    • 0042531982 scopus 로고    scopus 로고
    • For a Pd-only reaction, see
    • For a Pd-only reaction, see: Ma, S.; Yu, Z. J. Org. Chem. 2003, 68, 6149.
    • (2003) J. Org. Chem. , vol.68 , pp. 6149
    • Ma, S.1    Yu, Z.2
  • 12
    • 64749089011 scopus 로고    scopus 로고
    • We previously reported a series of Au/Pd cross-coupling reactions that were stoichiometric in Au and catalytic in Pd
    • We previously reported a series of Au/Pd cross-coupling reactions that were stoichiometric in Au and catalytic in Pd: Shi, Y.; Ramgren, S. D.; Blum, S. A. Organometallics 2009, 28, 1275.
    • (2009) Organometallics , vol.28 , pp. 1275
    • Shi, Y.1    Ramgren, S.D.2    Blum, S.A.3
  • 13
    • 72449134537 scopus 로고    scopus 로고
    • While the current manuscript was under revision, another example of a Au/Pd cross-coupling reaction that is also stoichiometric in Au and catalytic in Pd was reported
    • While the current manuscript was under revision, another example of a Au/Pd cross-coupling reaction that is also stoichiometric in Au and catalytic in Pd was reported: Hashmi, A. S. K.; Lothschütz, C.; Döpp, R.; Rudolph, M.; Ramamurthi, T. D.; Rominger, F. Angew. Chem., Int. Ed. 2009, 48, 1.
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 1
    • Hashmi, A.S.K.1    Lothschütz, C.2    Döpp, R.3    Rudolph, M.4    Ramamurthi, T.D.5    Rominger, F.6
  • 22
    • 33847633018 scopus 로고    scopus 로고
    • Recent reports from Nakao and Hiyama and from our group provide examples of the use of this mechanism as a unified concept for reaction design see ref 3 and: A previous example of this mechanistic phenomenon is the Sonogashira reaction (see ref 5)
    • Recent reports from Nakao and Hiyama and from our group provide examples of the use of this mechanism as a unified concept for reaction design (see ref 3 and: Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428) A previous example of this mechanistic phenomenon is the Sonogashira reaction (see ref 5).
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 2428
    • Nakao, Y.1    Yada, A.2    Ebata, S.3    Hiyama, T.4
  • 23
    • 72449164200 scopus 로고    scopus 로고
    • note
    • 2 did not result in product formation.
  • 25
    • 72449151475 scopus 로고    scopus 로고
    • note
    • -1 on the basis of triplicate runs at each loading level.
  • 27
    • 72449189363 scopus 로고    scopus 로고
    • note
    • We considered the possibility that cationic 2 rather than neutral 3 was the cross-coupling partner with 4. In the ethyl series, dealkylation of the oxonium ion did not occur, so we could query this point. Cationic ethyl 9 did not participate in cross-coupling, suggesting that neutral 3 rather than cationic 2 was the more likely transmetalation partner:
  • 29
    • 72449207312 scopus 로고    scopus 로고
    • note
    • 3 did not catalyze this transformation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.