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Volumn 132, Issue 6, 2010, Pages 2094-2098

Palladium-catalyzed intermolecular addition of formamides to alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; CATALYST SYSTEM; FORMAMIDES; HYDRIDOPALLADIUM; IN-SITU; INTERMOLECULAR ADDITIONS; INTERNAL ALKYNES; NORBORNENES; PALLADIUM CATALYST; REACTION CONDITIONS; TERMINAL ALKYNE; UNSATURATED AMIDES;

EID: 77249114737     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910038p     Document Type: Article
Times cited : (101)

References (49)
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    • a nd references cited therein
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    • Abbreviations: Xantphos, 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene; P(o-Tol)3, tri-ortho-tolylphosphine; PCy3, tricyclohexylphosphine; dppp, 1,3-bis(diphenylphosphino)propane; dppf, 1,1′-bis(diphenylphosphino) ferrocene; rac-BINAP, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl
    • 3, tricyclohexylphosphine; dppp, 1,3-bis(diphenylphosphino)propane; dppf, 1,1′-bis(diphenylphosphino) ferrocene; rac-BINAP, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl.
  • 30
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    • (a) Grushin, V. V. Chem. Rev. 1996, 96, 2011-2033.
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    • In the case of hexanoyl chloride, HCl may be afforded by a sequence of oxidative addition, decarbonylation. and β-hydrogen elimination as postulated in the literature.12 However, in the case of benzoyl chloride, β-hydrogen elimination from the resulting phenyl-palladium intermediate is not possible. Thus, the material balance after the reaction (entry 3 in Table 2) was analyzed by GC (eq i, As a result, 0.18 mmol of N,N-dimethylbenzamide was found as well as 3d (0.92 mmol, 92% yield) in the reaction mixture. Therefore, HCl was most likely generated by the reaction of benzoyl chloride (0.2 mmol) with 1a with concomitant formation of CO detected by GC, After the reaction, 0.76 mmol of 1a still remained, indicating further decommission of 1a did not occur substantially
    • 12 However, in the case of benzoyl chloride, β-hydrogen elimination from the resulting phenyl-palladium intermediate is not possible. Thus, the material balance after the reaction (entry 3 in Table 2) was analyzed by GC (eq i). As a result, 0.18 mmol of N,N-dimethylbenzamide was found as well as 3d (0.92 mmol, 92% yield) in the reaction mixture. Therefore, HCl was most likely generated by the reaction of benzoyl chloride (0.2 mmol) with 1a with concomitant formation of CO (detected by GC). After the reaction, 0.76 mmol of 1a still remained, indicating further decommission of 1a did not occur substantially.
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    • Wilkinson, G, Stone, F. G. A, Abel, E. W, Eds, Pergamon Press: New York
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    • (1982) Comprehensive Organometallic Chemistry , vol.8 , pp. 410-413
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    • 2H NMR measurements, 1e bearing the phenyl group was employed.
    • 2H NMR measurements, 1e bearing the phenyl group was employed.
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    • Negishi, E, de Meijere, A, Eds, Wiley-Interscience: New York
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    • Negishi, E.1
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.