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Volumn 47, Issue 26, 2008, Pages 4866-4869

Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters

Author keywords

Biaryls; Cleavage reactions; Cross coupling; Nickel; Suzuki Miyaura reaction

Indexed keywords

CHEMICAL REACTIONS; ESTERIFICATION; ESTERS; ETHERS; NAPHTHALENE;

EID: 50049090202     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801447     Document Type: Article
Times cited : (373)

References (45)
  • 1
    • 20544450502 scopus 로고    scopus 로고
    • For general reviews of metal-catalyzed cross-coupling reactions, see: a, Eds, A. de Meijere, F. Diederich, Wiley-VCH, Weinheim
    • For general reviews of metal-catalyzed cross-coupling reactions, see: a) Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
  • 11
  • 14
    • 34547789922 scopus 로고    scopus 로고
    • For an additional leading reference, see
    • For an additional leading reference, see: B. Saito, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 9602.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 9602
    • Saito, B.1    Fu, G.C.2
  • 27
    • 53549118762 scopus 로고    scopus 로고
    • Notes: a) The amount of PCy3 was not optimized for each substrate. In the reaction of p-acetylanisole (see Table 2, entry 6, the use of 20 mol% of PCy3 gave a inferior result (30% yield, Thus, we routinely conducted the reaction with 40 mol% of PCy3; b) When the corresponding pinacolate was used for the reaction in Table 2, entry 1, the yield of the product was decreased 20% yield
    • 3; b) When the corresponding pinacolate was used for the reaction in Table 2, entry 1, the yield of the product was decreased (20% yield).
  • 28
    • 53549118466 scopus 로고    scopus 로고
    • Oxidative addition of aryl methyl ethers in this catalysis may involve an intermediate in which the aromaticity of the aryl methyl ether is lost, such as η2-arene or Meisenheimer-type complexes. Polyaromatic compounds are expected to form such complexes more facilely, since part of the aromaticity is retained after complex formation
    • 2-arene or Meisenheimer-type complexes. Polyaromatic compounds are expected to form such complexes more facilely, since part of the aromaticity is retained after complex formation.
  • 32
    • 29844439845 scopus 로고    scopus 로고
    • Another possible explanation for the wider substrate scope in the cross-couplings with Grignard reagents is activation of C-O bonds by Lewis acidic magnesiumsalts. However, the addition of MgBr2, LiCl, and BPh3 in our system did not improve the reactivity of aryl methyl ethers. See: a N. Yoshikai, H. Mashima, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 17978;
    • 3 in our system did not improve the reactivity of aryl methyl ethers. See: a) N. Yoshikai, H. Mashima, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 17978;
  • 40
    • 27844437252 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 7216. See also references [12b] and [13a].
    • Angew. Chem. Int. Ed. 2005, 44, 7216. See also references [12b] and [13a].
  • 43
    • 40549128684 scopus 로고    scopus 로고
    • During preparation of this manuscript, another report on Kumada-type coupling of aryl methyl ethers with methylmagnesium halides was published: B.-T. Guan, S.-K. Xiang, T. Wu, Z.-P. Sun, B.-Q. Wang, K.-Q. Zhao, Z.-J. Shi, Chem. Commun. 2008, 1437.
    • During preparation of this manuscript, another report on Kumada-type coupling of aryl methyl ethers with methylmagnesium halides was published: B.-T. Guan, S.-K. Xiang, T. Wu, Z.-P. Sun, B.-Q. Wang, K.-Q. Zhao, Z.-J. Shi, Chem. Commun. 2008, 1437.
  • 45
    • 33845585240 scopus 로고    scopus 로고
    • A cross-coupling reaction between activated aryl fluorides and boronic acids has been reported: T. Schaub, M. Backes, U. Radius, J. Am. Chem. Soc. 2006, 128, 15964.
    • A cross-coupling reaction between activated aryl fluorides and boronic acids has been reported: T. Schaub, M. Backes, U. Radius, J. Am. Chem. Soc. 2006, 128, 15964.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.