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Volumn 17, Issue 13, 2015, Pages 3370-3373

P2Et Phosphazene: A Mild, Functional Group Tolerant Base for Soluble, Room Temperature Pd-Catalyzed C-N, C-O, and C-C Cross-Coupling Reactions

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Indexed keywords


EID: 84935133244     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01648     Document Type: Article
Times cited : (55)

References (38)
  • 15
    • 84935113438 scopus 로고    scopus 로고
    • note
    • 2Et.
  • 27
    • 84935070783 scopus 로고    scopus 로고
    • note
    • 5-Phenyl-3-bromopyridine 13 was used in place of 5 for the water couplings because the product was easier to quantify by UPLC analysis. Also, the aryl chloride and aryl iodide variants of 13 are not commercially available and were not interrogated.
  • 28
    • 84935053400 scopus 로고    scopus 로고
    • note
    • 2Et Phosphazene has been minimally used in transition metal catalysis, likely due to the current expense of this base. For many complex, sensitive synthetic targets in drug discovery or natural products synthesis, the cost of the reaction substrate prepared through multistep synthesis is much higher than this base cost.
  • 33
    • 84935144213 scopus 로고    scopus 로고
    • note
    • 2Et/tBuXPHOS with tert-amyl alcohol, conditions that were found to be most reactive for several reactions, also gave full conversion with 3-chloropyridine 14 and piperidine 7 in the presence of esters 16 and 17, with minimal ester decomposition.
  • 38
    • 84935136678 scopus 로고    scopus 로고
    • note
    • The couplings of amines 6 (with Brettphos Pd G3) and 7 (with RuPhos Pd G2) with bromide 13 have not been reported in the literature at room temperature, so we independently verified that LiHMDS is indeed capable of coupling these nucleophiles at rt (5% catalyst, THF, 1.5 equiv of nucleophile, 2 equiv of base, 18 h).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.