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Volumn 133, Issue 28, 2011, Pages 10999-11005

Rational catalysis design on the basis of mechanistic understanding: Highly efficient Pd-catalyzed cyanation of aryl bromides with NaCN in recyclable solvents

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC BROMIDES; ARYL BROMIDES; CATALYTIC REACTIONS; CYANATION; CYANATION REACTION; ISOLATED YIELD; PD CATALYST;

EID: 79960245046     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2042035     Document Type: Article
Times cited : (167)

References (72)
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    • Independently and simultaneously, Cassar reported the first Ni-catalyzed aromatic cyanation reaction. See
    • Independently and simultaneously, Cassar reported the first Ni-catalyzed aromatic cyanation reaction. See: Cassar, L. J. Organomet. Chem. 1973, 54, C57
    • (1973) J. Organomet. Chem. , vol.54 , pp. 57
    • Cassar, L.1
  • 15
    • 79960248887 scopus 로고    scopus 로고
    • It is worth to emphasize that, against the common belief of many researchers in academia, KCN and especially even less costly NaCN, in spite of their toxicity, are by far the most preferred industrial sources of cyanide for reaction 1.
    • It is worth to emphasize that, against the common belief of many researchers in academia, KCN and especially even less costly NaCN, in spite of their toxicity, are by far the most preferred industrial sources of cyanide for reaction 1.
  • 28
    • 3743119954 scopus 로고
    • For selected reports and review articles, see: Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031
    • (1988) Chem. Rev. , vol.88 , pp. 1031
    • Brown, J.M.1    Cooley, N.A.2
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    • Eur. Pat. Appl. EP 0802173.
    • Nishiyama, M.; Koie, Y. Eur. Pat. Appl. EP 0802173, 1997.
    • (1997)
    • Nishiyama, M.1    Koie, Y.2
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    • 79960217944 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 2008/128644.
    • Walter, R.; Meyer, H.; Voss, S. PCT Int. Appl. WO 2008/128644, 2008.
    • (2008)
    • Walter, R.1    Meyer, H.2    Voss, S.3
  • 56
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    • -1 at 60 °C). (19) At the beginning of the runs, the solution also contained 0.42 mL of PhBr where NaCN is virtually insoluble. Furthermore, as the reaction occurred, the polarity of the liquid phase was changing due to the consumption of bromobenzene and the simultaneous formation of more polar benzonitrile and NaBr. All these factors, however, are unlikely to change significantly the solubility of NaCN in the liquid phase consisting of mostly acetonitrile (ca. 74-84% by volume).
    • -1 at 60 °C). (19) At the beginning of the runs, the solution also contained 0.42 mL of PhBr where NaCN is virtually insoluble. Furthermore, as the reaction occurred, the polarity of the liquid phase was changing due to the consumption of bromobenzene and the simultaneous formation of more polar benzonitrile and NaBr. All these factors, however, are unlikely to change significantly the solubility of NaCN in the liquid phase consisting of mostly acetonitrile (ca. 74-84% by volume).
  • 58


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.