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Volumn 131, Issue 14, 2009, Pages 5044-5045

Mechanistic study of copper-catalyzed aerobic oxidative coupling of arylboronic esters and methanol: Insights into an organometallic oxidase reaction

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; ARYLBORONIC ACIDS; C-O BOND FORMATION; HETEROATOM; HETEROATOM BONDS; LIMITING STEP; MECHANISTIC ANALYSIS; MECHANISTIC STUDIES; OXIDASE REACTION; OXIDATIVE COUPLINGS; RE-OXIDATION; REDUCED CATALYSTS; SPECTROSCOPIC STUDIES; TRANSMETALATION;

EID: 67849106811     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9006657     Document Type: Article
Times cited : (339)

References (31)
  • 2
    • 33947476790 scopus 로고
    • (b) Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321.
    • (1962) J. Org. Chem , vol.27 , pp. 3320-3321
    • Hay, A.S.1
  • 12
    • 27644475970 scopus 로고    scopus 로고
    • Hall, D. G, Ed, Wiley- VCH: Weinheim
    • Chan, D. M. T.; Lam, P. Y. S. In Boronic Acids; Hall, D. G., Ed.; Wiley- VCH: Weinheim, 2005; pp 205-240.
    • (2005) Boronic Acids , pp. 205-240
    • Chan, D.M.T.1    Lam, P.Y.S.2
  • 19
    • 67849127110 scopus 로고    scopus 로고
    • Lam et al. have demonstrated via 18O-labeling studies that a phenol byproduct arises from water serving as an oxygen nucleophile, not via oxygen-atom transfer from O2: Lam, P. Y. S.; Bonne, D.; Vincent, G.; Clark, C. G.; Combs, A. P. Tetrahedron Lett. 2003, 44, 1691-1694.
    • Lam et al. have demonstrated via 18O-labeling studies that a phenol byproduct arises from water serving as an oxygen nucleophile, not via oxygen-atom transfer from O2: Lam, P. Y. S.; Bonne, D.; Vincent, G.; Clark, C. G.; Combs, A. P. Tetrahedron Lett. 2003, 44, 1691-1694.
  • 20
    • 67849129013 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 23
    • 24944468108 scopus 로고    scopus 로고
    • (b) Stahl, S. S. Science 2005, 309, 1824-1826.
    • (2005) Science , vol.309 , pp. 1824-1826
    • Stahl, S.S.1
  • 24
    • 67849111878 scopus 로고    scopus 로고
    • Three similar CuII species are evident under catalytic conditions; see Figure S2 for experimental and simulated EPR data. Very similar EPR spectra are obtained from solutions of Cu(OAc)2 and B(OMe)3 in methanol. In contrast, Cu(OAc)2 alone in methanol exists as a dimer that exhibits virtually no EPR signal (cf.: Rao, V. M.; Sathyanarayana, D. N.; Manohar, H. Ind. J. Chem. Sect. A1985, 24A, 417-418).
    • Three similar CuII species are evident under catalytic conditions; see Figure S2 for experimental and simulated EPR data. Very similar EPR spectra are obtained from solutions of Cu(OAc)2 and B(OMe)3 in methanol. In contrast, Cu(OAc)2 alone in methanol exists as a dimer that exhibits virtually no EPR signal (cf.: Rao, V. M.; Sathyanarayana, D. N.; Manohar, H. Ind. J. Chem. Sect. A1985, 24A, 417-418).
  • 25
    • 67849130884 scopus 로고    scopus 로고
    • See, for example, refs 3c and 5
    • See, for example, refs 3c and 5.
  • 29
    • 24344461366 scopus 로고    scopus 로고
    • Xifra, R.; Ribas, X.; Llobet, A.; Poater, A.; Duran, M.; Solà, M.; Stack, T. D. P.; Benet-Buchholz, J.; Donnadieu, B.; Mahía, J.; Parella, T. Chem.sEur. J. 2005, 11, 5146-5156.
    • (b) Xifra, R.; Ribas, X.; Llobet, A.; Poater, A.; Duran, M.; Solà, M.; Stack, T. D. P.; Benet-Buchholz, J.; Donnadieu, B.; Mahía, J.; Parella, T. Chem.sEur. J. 2005, 11, 5146-5156.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.