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Volumn 76, Issue 9, 2011, Pages 3016-3023

N-heterocyclic carbene-mediated oxidative esterification of aldehydes: Ester formation and mechanistic studies

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDE; CINNAMYL BROMIDE; ELECTRON-DEFICIENT; ESTER FORMATION; GOOD YIELD; ISOTOPIC LABELING; MECHANISTIC STUDIES; N-HETEROCYCLIC CARBENES; PLAUSIBLE MECHANISMS; UNSATURATED ALDEHYDES;

EID: 79955559516     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200275c     Document Type: Article
Times cited : (103)

References (96)
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    • The term "activated carboxylates" is well-known in literature. See:;, This means free carboxylic acid needs to be activated for transformation to esters and amides through conversion to acyl chlorides, mixed anhydrides, or carbodiimides and other expensive coupling reagents.; In Houben-Weyl: Methoden der Organischen, 4 th ed.; Thieme: Stuttgart, 1995; p 656.
    • The term "activated carboxylates" is well-known in literature. See: Chow, K. Y-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126 This means free carboxylic acid needs to be activated for transformation to esters and amides through conversion to acyl chlorides, mixed anhydrides, or carbodiimides and other expensive coupling reagents. Carbonsaeuren und Carbonsaeurederivative; Falbe, J. In Houben-Weyl: Methoden der Organischen, 4 th ed.; Thieme: Stuttgart, 1995; p 656.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8126
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  • 3
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    • Reagents for High-Throughput solid-phase and solution-phase Organic Synthesis
    • Wiley: New York
    • Reagents for High-Throughput solid-phase and solution-phase Organic Synthesis; Wipf, P. In Handbook of Reagents for Organic Synthesis; Wiley: New York, 2005.
    • (2005) Handbook of Reagents for Organic Synthesis
    • Wipf, P.1
  • 9
    • 53849129886 scopus 로고    scopus 로고
    • See the review and references cited therein
    • See the review and references cited therein: Ekoue-Kovi, K.; Wolf, C. Chem. - Eur. J. 2008, 14, 6302
    • (2008) Chem. - Eur. J. , vol.14 , pp. 6302
    • Ekoue-Kovi, K.1    Wolf, C.2
  • 27
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    • By using metal-based oxidants, see:;, and references cited therein
    • By using metal-based oxidants, see: Maki, B. E.; Chan, A.; Philips, E. M.; Scheidt, K. A. Tetrahedron 2009, 65, 3102 and references cited therein
    • (2009) Tetrahedron , vol.65 , pp. 3102
    • Maki, B.E.1    Chan, A.2    Philips, E.M.3    Scheidt, K.A.4
  • 38
    • 77950197170 scopus 로고    scopus 로고
    • For reviews on NHC-organocatalysis, see
    • For reviews on NHC-organocatalysis, see: Moore, J. L.; Rovis, T. Top. Curr. Chem. 2009, 291, 77
    • (2009) Top. Curr. Chem. , vol.291 , pp. 77
    • Moore, J.L.1    Rovis, T.2
  • 71
    • 79955550022 scopus 로고    scopus 로고
    • note
    • 2 was used as an oxidant, another important pathway is also not overruled, where allyic alcohol was generated in situ from the allyl bromide and reacted with acyl benzimidazolium intermediate II (Scheme 5) to provide ester 5.
  • 72
    • 67650378952 scopus 로고    scopus 로고
    • 2 (balloon) as oxidant
    • 2 (balloon) as oxidant: Goswami, S.; Hazra, A. Chem. Lett. 2009, 38, 484
    • (2009) Chem. Lett. , vol.38 , pp. 484
    • Goswami, S.1    Hazra, A.2
  • 73
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    • NHC-catalyzed synthesis of acid from aldehydes via internal redox processes:; J. Am. Chem. Soc. 2010, 132, 914
    • Yoshida, M.; Katagiri, Y.; Zhu, W.-B.; Shishido, K. Org. Biomol. Chem. 2009, 7, 4062 NHC-catalyzed synthesis of acid from aldehydes via internal redox processes: Gu, L.; Zhang, Y. J. Am. Chem. Soc. 2010, 132, 914
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 4062
    • Yoshida, M.1    Katagiri, Y.2    Zhu, W.-B.3    Shishido, K.4    Gu, L.5    Zhang, Y.6
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.