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Volumn 68, Issue 14, 2003, Pages 5750-5753

Increasing rates and scope of reactions: Sluggish amines in microwave-heated aminocarbonylation reactions under air

Author keywords

[No Author keywords available]

Indexed keywords

MICROWAVE IRRADIATION;

EID: 0038337744     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034382d     Document Type: Article
Times cited : (243)

References (34)
  • 1
    • 0003670259 scopus 로고    scopus 로고
    • Fenniri, H., Ed.; Oxford University Press: Oxford, New York
    • Combinatorial Chemistry: A Practical Approach; Fenniri, H., Ed.; Oxford University Press: Oxford, New York, 2000.
    • (2000) Combinatorial Chemistry: A Practical Approach
  • 23
    • 0038400124 scopus 로고    scopus 로고
    • note
    • Investigation of the reaction parameters showed that the choice of base was crucial in the aminocarbonylation of 2-iodotoluene with aniline. Inorganic carbonate bases and tertiary aliphatic amines were nonproductive at the temperatures investigated here (50-150 °C). The nucleophilic catalysts imidazole and DMAP were effective at high temperatures (150 °C), but the use of DBU as base furnished a dramatically improved reaction rate, which allowed substantially lower temperatures. Palladium acetate afforded a slightly superior catalytic system compared to Pd/C and phosphine containing pre-catalysts. The etherous solvents diglyme, DME, dioxane, and THF were all more efficient than DMF, MeCN, or toluene. THF was the preferred choice because of the easy access to freshly distilled solvent and the simple removal from the reaction mixture.
  • 25
    • 0038061850 scopus 로고    scopus 로고
    • note
    • Optical rotation compared to commercially available sample (Fluka).
  • 32
    • 0038400122 scopus 로고    scopus 로고
    • note
    • 2, was responsible for the immediate CO-release illustrated in Figure 1, profile B. The omission of 1d or 2b did not affect the pressure.
  • 33
    • 0038400120 scopus 로고    scopus 로고
    • note
    • Using aqueous potassium carbonate, triethylamine, 1,2,2,6,6-pentamethylpiperidine, or 2c as base in the aminocarbonylation of 1d with 2c at 100 °C, 15 min, afforded less than 10% conversion of 1d and little or no increase in pressure. DMAP was able to release CO, but the conversion was still low under these conditions.
  • 34
    • 0003877758 scopus 로고    scopus 로고
    • Lide, D. R., Ed.; CRC Press: Boca Raton, FL
    • CRC Handbook of Chemistry and Physics, 83rd ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2002; pp 3-384, 4-43.
    • (2002) Handbook of Chemistry and Physics, 83rd Ed. , pp. 3-384


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.