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Volumn 46, Issue 33, 2007, Pages 6350-6353

Phenanthroline ligands in aryl palladium hydrazinato complexes: Catalysts for efficient coupling of azo componds with aryl boronic acids

Author keywords

Amides; Aryl boronic acids; Coupling reactions; Hydrazines; Palladium

Indexed keywords

AMIDES; CATALYSTS; HYDRAZINE; LIGANDS; SYNTHESIS (CHEMICAL);

EID: 34548217139     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700288     Document Type: Article
Times cited : (44)

References (36)
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    • c) Top. Curr. Chem. 2002, 219 (Ed.: N. Miyaura);
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    • For reviews, see: a) J. F. Hartwig, Synlett 2006, 1283;
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    • For the problem of Pd-catalyzed amidation with simple hydrazines, hydrazides, and carbamate-protected hydrazines, see
    • For the problem of Pd-catalyzed amidation with simple hydrazines, hydrazides, and carbamate-protected hydrazines, see Ref. [3a].
    • , vol.3 a
    • Ref1
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    • For the role of phenanthroline ligands in Heck couplings, see: a
    • For the role of phenanthroline ligands in Heck couplings, see: a) W. Cabri, L. Candiani, A. Bedeschi, A. Santi, J. Org. Chem. 1993, 58, 7421;
    • (1993) J. Org. Chem , vol.58 , pp. 7421
    • Cabri, W.1    Candiani, L.2    Bedeschi, A.3    Santi, A.4
  • 27
    • 0032506574 scopus 로고    scopus 로고
    • For mechanistically nonrelated uncatalyzed reactions of metalated aromatics with azodicarboxylates, see: a R. Velarde-Ortiz, A. Guijarro, R. D. Rieke, Tetrahedron Lett. 1998, 39, 9157, and references therein;
    • For mechanistically nonrelated uncatalyzed reactions of metalated aromatics with azodicarboxylates, see: a) R. Velarde-Ortiz, A. Guijarro, R. D. Rieke, Tetrahedron Lett. 1998, 39, 9157, and references therein;
  • 29
    • 26844546122 scopus 로고    scopus 로고
    • mechanistically non-related copper-catalyzed variant: T. Uemura, N. Chatani, J. Org. Chem. 2005, 70, 8631.
    • c) mechanistically non-related copper-catalyzed variant: T. Uemura, N. Chatani, J. Org. Chem. 2005, 70, 8631.
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    • 0002812967 scopus 로고    scopus 로고
    • For aryl-aryl coupling reactions that use oxygen as the oxidant, see: a
    • For aryl-aryl coupling reactions that use oxygen as the oxidant, see: a) N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59;
    • (2002) Top. Curr. Chem , vol.219 , pp. 11-59
    • Miyaura, N.1
  • 32
    • 34548252490 scopus 로고    scopus 로고
    • unpublished control experiments from our research group show that palladadiaziridines ligated with diphenylphosphinoferrocene (dppf) and 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl (binap) accept two aryl groups from aryl boronic acids and liberate free 1,2-dicarbamoylhydrazine; azodicarboxylates serve as a simple reoxidant in these processes, comparable to oxygen in the aerobic variant.
    • c) unpublished control experiments from our research group show that palladadiaziridines ligated with diphenylphosphinoferrocene (dppf) and 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl (binap) accept two aryl groups from aryl boronic acids and liberate free 1,2-dicarbamoylhydrazine; azodicarboxylates serve as a simple reoxidant in these processes, comparable to oxygen in the aerobic variant.
  • 34
    • 34548260908 scopus 로고    scopus 로고
    • Extensive mechanistic investigation for the detection of intermediates of type B, as well as synthetic approaches toward their isolation are currently being carried out.
    • Extensive mechanistic investigation for the detection of intermediates of type B, as well as synthetic approaches toward their isolation are currently being carried out.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.