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Volumn 132, Issue 2, 2010, Pages 466-467

Pd-catalyzed intramolecular acylation of aryl bromides via C-H functionalization: A highly efficient synthesis of benzocyclobutenones

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; C-H FUNCTIONALIZATION; CATALYST SYSTEM; CHEMICAL EQUATIONS; EFFICIENT SYNTHESIS; FUNCTIONALIZED; SUBSTITUTION PATTERNS;

EID: 74949109727     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja909811t     Document Type: Article
Times cited : (120)

References (39)
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    • Selected references: (a) Suzuki, T.; Hamura, T.; Suzuki, K. Angew. Chem., Int. Ed. 2008, 47, 2248.
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    • published ASAP online Oct 29, DOI: 10.1021/cr900096x
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    • (2009) Chem. Rev
    • Willis, M.C.1
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    • For an excellent review of related carbometallation studies, see
    • For an excellent review of related carbometallation studies, see: Larock, R. C. J. Organomet. Chem. 1999, 576, 111.
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    • Larock, R.C.1
  • 18
    • 33845207951 scopus 로고    scopus 로고
    • For an elegant method using acyl anion equivalents, see
    • For an elegant method using acyl anion equivalents, see: Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 14800.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 14800
    • Takemiya, A.1    Hartwig, J.F.2
  • 22
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    • For related stochiometric aldehyde insertions into the Rh-aryl bond, see: a
    • For related stochiometric aldehyde insertions into the Rh-aryl bond, see: (a) Krug, C.; Hartwig, J. F. Organometallics 2004, 23, 4594.
    • (2004) Organometallics , vol.23 , pp. 4594
    • Krug, C.1    Hartwig, J.F.2
  • 27
    • 0034249671 scopus 로고    scopus 로고
    • A related 4-endo-trig cyclization under the conditions reported in ref 10 or 11 cannot occur because the double bond would not be flexible enough to bend in the proper conformation for the Heck-type coupling. See: Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
    • A related 4-endo-trig cyclization under the conditions reported in ref 10 or 11 cannot occur because the double bond would not be flexible enough to bend in the proper conformation for the Heck-type coupling. See: Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
  • 29
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    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 31
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    • The reaction of aldehydes with α-hydrogens led to decomposition. Similar behavior was found in other related processes see ref 16
    • The reaction of aldehydes with α-hydrogens led to decomposition. Similar behavior was found in other related processes (see ref 16).
  • 32
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    • For selected insertions of Pd oxidative addition complexes across the C=O bond, see: (a) Ketones: Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827.
    • For selected insertions of Pd oxidative addition complexes across the C=O bond, see: (a) Ketones: Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827.
  • 33
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    • Aldehydes: Zhao, Y. B.; Mariampillai, B.; Candito, D. A.; Laleu, B.; Li, M. Z.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 1849.
    • (b) Aldehydes: Zhao, Y. B.; Mariampillai, B.; Candito, D. A.; Laleu, B.; Li, M. Z.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 1849.
  • 34
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    • Esters: Solé, D.; Serrano, O. J. Org. Chem. 2008, 73, 9372.
    • (c) Esters: Solé, D.; Serrano, O. J. Org. Chem. 2008, 73, 9372.
  • 35
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    • Anhydrides: Cacchi, S.; Fabrizi, G.; Gavazza, F.; Goggiamani, A. Org. Lett. 2003, 5, 289.
    • (d) Anhydrides: Cacchi, S.; Fabrizi, G.; Gavazza, F.; Goggiamani, A. Org. Lett. 2003, 5, 289.
  • 39
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    • At present, we cannot rule out the intermediacy of acyl palladium intermediates via 1,4-palladium migration see ref 18
    • At present, we cannot rule out the intermediacy of acyl palladium intermediates via 1,4-palladium migration (see ref 18).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.