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Volumn 76, Issue 1, 2011, Pages 170-180

A palladium-catalyzed multicomponent synthesis of imidazolinium salts and imidazolines from imines, acid chlorides, and carbon monoxide

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; FUNCTIONALIZED IMINES; GOOD YIELD; IMIDAZOLINES; IMIDAZOLINIUM; IMIDAZOLINIUM SALTS; IN-SITU; INDEPENDENT CONTROL; MULTICOMPONENT SYNTHESIS; PALLADIUM CATALYST; PROTONATED;

EID: 78650884340     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101858d     Document Type: Article
Times cited : (47)

References (87)
  • 73
    • 78650875972 scopus 로고    scopus 로고
    • In addition to enhancing the reaction rate, catalysis with bulky phosphines proceeds rapidly with the 2:1 imine:acid chloride ratio, rather than the excess acid chloride employed with bipyridine ligands. While the reason for this effect is as yet unclear, we postulate that the second imine acts as a base to accelerate HCl elimination.
    • In addition to enhancing the reaction rate, catalysis with bulky phosphines proceeds rapidly with the 2:1 imine:acid chloride ratio, rather than the excess acid chloride employed with bipyridine ligands. While the reason for this effect is as yet unclear, we postulate that the second imine acts as a base to accelerate HCl elimination.
  • 74
    • 78650857667 scopus 로고    scopus 로고
    • All products were formed as a single diastereomer and consistent with the trans orientation of the aryl groups previously noted. (20)
    • All products were formed as a single diastereomer and consistent with the trans orientation of the aryl groups previously noted. (20)
  • 75
    • 78650859930 scopus 로고    scopus 로고
    • For example, enolizable imines rapidly generate enamides from iminiium salts 1. BnN=C(H) t -Bu has been previously employed to generate Münchnones, (22) but they are presumably too bulky to allow subsequent dipolar cycloaddition.
    • For example, enolizable imines rapidly generate enamides from iminiium salts 1. BnN=C(H) t -Bu has been previously employed to generate Münchnones, (22) but they are presumably too bulky to allow subsequent dipolar cycloaddition.
  • 82
    • 78650865139 scopus 로고    scopus 로고
    • It is necessary to introduce a methyl ester protecting group before nitrogen deprotection; otherwise, decarboxylation of the parent compound is observed.
    • It is necessary to introduce a methyl ester protecting group before nitrogen deprotection; otherwise, decarboxylation of the parent compound is observed.
  • 86
    • 78650899559 scopus 로고    scopus 로고
    • Celite filtration was performed when palladium black formed in the crude solution. If the brine wash is neglected, unidentified phosphine species contaminate the products and are very difficult to remove.
    • Celite filtration was performed when palladium black formed in the crude solution. If the brine wash is neglected, unidentified phosphine species contaminate the products and are very difficult to remove.
  • 87
    • 78650874258 scopus 로고    scopus 로고
    • 3 or wet organic solvents. Decarboxylation to 4,5-dihydroimidazolinium salts is commonly observed when these precautions are not taken. Similarly, precipitation at -35 °C and collection of the precipitate should be conducted with care under a dry atmosphere as condensation of water vapor from the air can elicit the same decomposition.
    • 3 or wet organic solvents. Decarboxylation to 4,5-dihydroimidazolinium salts is commonly observed when these precautions are not taken. Similarly, precipitation at -35 °C and collection of the precipitate should be conducted with care under a dry atmosphere as condensation of water vapor from the air can elicit the same decomposition.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.