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Volumn 76, Issue 11, 2011, Pages 4552-4563

A general method for palladium-catalyzed reactions of primary sulfonamides with aryl nonaflates

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYST; ELECTRON-RICH; GENERAL METHOD; HIGH YIELD; KINETIC DATA; PALLADIUM-CATALYZED REACTIONS; PHOSPHINE LIGANDS; RATE-LIMITING STEPS; REACTION CONDITIONS; REDUCTIVE ELIMINATION; SULFONAMIDATION; TERT-AMYL ALCOHOLS;

EID: 79957864278     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200443u     Document Type: Article
Times cited : (83)

References (66)
  • 12
    • 79957868143 scopus 로고    scopus 로고
    • See refs 13 and 14 for examples of Pd-catalyzed reactions of aryl halides/psuedohalides with secondary sulfonamides and ref 15 for examples of intramolecular Cu-catalyzed reaction of aryl triflates with sulfonamides
    • See refs 13 and 14 for examples of Pd-catalyzed reactions of aryl halides/psuedohalides with secondary sulfonamides and ref 15 for examples of intramolecular Cu-catalyzed reaction of aryl triflates with sulfonamides.
  • 17
    • 79957837014 scopus 로고    scopus 로고
    • We have found that aryl nonaflates can be cleanly prepared from the parent phenols using nonafluorobutanesulfonyl fluoride in acetonitrile in the presence of 325-mesh potassium carbonate as the stoichiometric base
    • We have found that aryl nonaflates can be cleanly prepared from the parent phenols using nonafluorobutanesulfonyl fluoride in acetonitrile in the presence of 325-mesh potassium carbonate as the stoichiometric base.
  • 18
    • 79957837945 scopus 로고    scopus 로고
    • See ref 13 for a detailed account of Pd-catalyzed couplings of aryl nonaflates with secondary sulfonamides
    • See ref 13 for a detailed account of Pd-catalyzed couplings of aryl nonaflates with secondary sulfonamides.
  • 19
    • 79957825294 scopus 로고    scopus 로고
    • 3 was used as base
    • 3 was used as base.
  • 20
    • 79957852118 scopus 로고    scopus 로고
    • The product was not isolated and the reported yield is an approximate yield based on HPLC
    • The product was not isolated and the reported yield is an approximate yield based on HPLC.
  • 21
    • 79957873264 scopus 로고    scopus 로고
    • The coupled product was formed in 6% yield after 16 h at 80 °C in the absence of palladium and ligand
    • The coupled product was formed in 6% yield after 16 h at 80 °C in the absence of palladium and ligand.
  • 22
    • 79957852575 scopus 로고    scopus 로고
    • Acyl substituted aryl bromide or aryl triflate were found to be unsuitable substrates for Pd-catalyzed amidation reaction due to a competitive ketone arylation reaction. See ref 3
    • Acyl substituted aryl bromide or aryl triflate were found to be unsuitable substrates for Pd-catalyzed amidation reaction due to a competitive ketone arylation reaction. See ref 3.
  • 25
    • 79957848199 scopus 로고    scopus 로고
    • Oxidative addition may become the rate-limiting step at low concentrations of aryl chlorides
    • Oxidative addition may become the rate-limiting step at low concentrations of aryl chlorides.
  • 29
    • 79957808690 scopus 로고    scopus 로고
    • -3 mM/min, and the reaction proceeded to approximately 70% conversion after 24 h. Perhaps the rate-limiting step changes for the reactions of chloroarenes. The discussion of chloroarenes as electrophile is beyond the scope of the current study
    • -3 mM/min, and the reaction proceeded to approximately 70% conversion after 24 h. Perhaps the rate-limiting step changes for the reactions of chloroarenes. The discussion of chloroarenes as electrophile is beyond the scope of the current study.
  • 44
    • 79957837468 scopus 로고    scopus 로고
    • Milled to particle size with d90 = 420 μm
    • Milled to particle size with d90 = 420 μm.
  • 45
    • 79957813001 scopus 로고    scopus 로고
    • 4 for 30 min before addition of substrates was needed to obtain reproducible reaction rate and yield in certain cases; however, this operation is not necessary. Reactions can also be performed by following the general procedure reported for the entries in Table 1
    • 4 for 30 min before addition of substrates was needed to obtain reproducible reaction rate and yield in certain cases; however, this operation is not necessary. Reactions can also be performed by following the general procedure reported for the entries in Table 1.
  • 46
    • 79957840731 scopus 로고    scopus 로고
    • 4 is required for this reaction
    • 4 is required for this reaction.
  • 60
    • 79957853154 scopus 로고    scopus 로고
    • 13C NMR spectroscopy. Furthermore, this material melted at 96-97 °C. We suspect that in the original report by King et al. an impurity is responsible for the depressed melting point they observe
    • 13C NMR spectroscopy. Furthermore, this material melted at 96-97 °C. We suspect that in the original report by King et al. an impurity is responsible for the depressed melting point they observe.
  • 62
    • 79957816225 scopus 로고    scopus 로고
    • 13C NMR spectroscopy. Furthermore, this material melted at 96.3-97.2 °C. Given that no procedure for the preparation or purification of 4-methoxy- N - p -tolylbenzenesulfonamide is given in ref 61, we cannot rule out the possibility that they isolated a higher melting solvate or polymorph, but we suspect that the high melting point reported for this compound is in error
    • 13C NMR spectroscopy. Furthermore, this material melted at 96.3-97.2 °C. Given that no procedure for the preparation or purification of 4-methoxy- N-p -tolylbenzenesulfonamide is given in ref 61, we cannot rule out the possibility that they isolated a higher melting solvate or polymorph, but we suspect that the high melting point reported for this compound is in error.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.