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Volumn 130, Issue 45, 2008, Pages 15157-15166

Synthesis of benzocyclobutenes by palladium-catalyzed C-H activation of methyl groups: Method and mechanistic study

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; BROMINE; CARBON; CARBOXYLATION; CHEMICAL ACTIVATION; PALLADIUM; POTASH; SUBSTRATES;

EID: 57349192903     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805598s     Document Type: Article
Times cited : (257)

References (116)
  • 1
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    • Selected reviews: (a) Dyker, G
    • Selected reviews: (a) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
    • (1999) Angew. Chem., Int. Ed , vol.38 , pp. 1698
  • 5
    • 57349161130 scopus 로고    scopus 로고
    • In this article, C-H activation refers to transition-metal-catalyzed reactions that involve the cleavage of a C-H bond by an inner-sphere mechanism (see ref 1c, This definition excludes reactions that involve an outer-sphere mechanism, such as C-H insertions: (a) Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A, Ed, Wiley-VCH: Weinheim, 2005
    • In this article, C-H activation refers to transition-metal-catalyzed reactions that involve the cleavage of a C-H bond by an inner-sphere mechanism (see ref 1c). This definition excludes reactions that involve an outer-sphere mechanism, such as C-H insertions: (a) Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005.
  • 27
    • 18744372130 scopus 로고    scopus 로고
    • Recent work in allylic C-H activation: (a) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
    • Recent work in allylic C-H activation: (a) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
  • 69
    • 57349170666 scopus 로고    scopus 로고
    • 4 combination is economically advantageous and at this temperature using 10 mol% palladium(0) was necessary to ensure a reproducible yield.
    • 4 combination is economically advantageous and at this temperature using 10 mol% palladium(0) was necessary to ensure a reproducible yield.
  • 98
    • 57349124729 scopus 로고    scopus 로고
    • The low level of incorporation, compared to the amount of abnormal regioisomer observed with substituents para to the bromine and in particular with fluorine Table 2, entry 21, might reflect a tendency of electron-withdrawing substituents to favour the 17c → 3 pathway: see refs 20c, e, and 23. Alternatively, an intermolecular H/D exchange with traces of water or another protic source could be operating: see ref 26e
    • The low level of incorporation, compared to the amount of "abnormal" regioisomer observed with substituents para to the bromine and in particular with fluorine (Table 2, entry 21), might reflect a tendency of electron-withdrawing substituents to favour the 17c → 3 pathway: see refs 20c, e, and 23. Alternatively, an intermolecular H/D exchange with traces of water or another protic source could be operating: see ref 26e.
  • 108
    • 35548984895 scopus 로고    scopus 로고
    • Gaussian 03
    • Pople, J. A. et al. Gaussian 03, revision C.02; 2003.
    • (2003) revision , Issue.C.02
    • Pople, J.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.