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Volumn 63, Issue 35, 2007, Pages 8598-8608

Catalytic nucleophilic activation of acetonitrile via a cooperative catalysis of cationic Ru complex, DBU, and NaPF6

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALDEHYDE DERIVATIVE; AMINE; KETONE DERIVATIVE; RUTHENIUM COMPLEX; SODIUM DERIVATIVE;

EID: 34447513871     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.04.051     Document Type: Article
Times cited : (57)

References (124)
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    • tBu:
  • 66
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    • tOBu:
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    • For general reviews of CpRu complex, see:
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    • For preparation of 3a, see:
  • 90
    • 34447578433 scopus 로고    scopus 로고
    • note
    • DBN was used as base. DBN proved to be effective with 3b whereas yield was slightly worse than that obtained with DBU.
  • 92
    • 34447552187 scopus 로고    scopus 로고
    • Using bromoacetonitrile, see:
  • 94
    • 34447541855 scopus 로고    scopus 로고
    • Using trimethylsilylacetonitrile, see:
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    • note
    • See Supplementary data.
  • 106
    • 34447562396 scopus 로고    scopus 로고
    • note
    • Ab initio calculation shows a substantial portion of the negative charge resides at the carbon atom in α-cyano carbanions, suggesting that metalated acetonitrile is less likely in the tautomeric ketenimide form (Ref. 6b). See also Ref. 5c.
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    • note
    • Details are summarized in Section 4.
  • 108
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    • note
    • 31P NMR analysis.
  • 109
    • 34447541854 scopus 로고    scopus 로고
    • note
    • 31P NMR analysis. See also Section 4.
  • 112
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    • Toy, P. H.; Janda, K. D. Abstracts, 219th ACS national meeting, San Francisco, 2000, ORGN-432.
  • 113
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    • note
    • *Ru complex exhibited inferior performance in the reaction with 1a.
  • 114
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    • note
    • 6 resulted in the worse result.
  • 115
    • 34447533987 scopus 로고    scopus 로고
    • note
    • Trace amounts of dehydrated product are observed occasionally.
  • 118
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    • note
    • The addition to acetone and cyclohexanone derivative was reported in Ref. 10a using strongly basic proazaphosphatrane base.
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    • For reviews, see:
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    • note
    • 6.
  • 124
    • 34447553140 scopus 로고    scopus 로고
    • note
    • For an example of catalytic cyanomethylation of trifluoroacetophenone (11a) with trimethylsilylacetonitrile, see Ref. 32b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.