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Volumn 47, Issue 29, 2008, Pages 5430-5433

Palladium catalyzed synthesis of münchnones from α-amidoethers: A mild route to pyrroles

Author keywords

C O activation; Dipolar cycloaddition; Palladium; Pyrrole

Indexed keywords

ACETYLENE; CARBONYLATION; CHEMICAL REACTIONS; CYCLOADDITION; HYDROCARBONS; OXYGEN; PALLADIUM;

EID: 49149131939     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801385     Document Type: Article
Times cited : (121)

References (37)
  • 3
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    • Angew. Chem. Int. Ed. 2000, 39, 1010-1027;
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 1010-1027
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    • Amidocarbonylation can proceed in the absence of acid cocatalysts, though yields are reduced and pressing conditions required: M. Beller, M. Eckert, F. Vollmüller, J. Mol. Catal. A 1998, 135, 23-33.
    • Amidocarbonylation can proceed in the absence of acid cocatalysts, though yields are reduced and pressing conditions required: M. Beller, M. Eckert, F. Vollmüller, J. Mol. Catal. A 1998, 135, 23-33.
  • 13
    • 53549123362 scopus 로고    scopus 로고
    • This acid mediated C-O activation is similar to other carbonylations of ethers/alcohols: a V. Mahadevan, Y. D. Y. L. Getzler, G. W. Coates, Angew. Chem. 2002, 114, 2905-2908;
    • This acid mediated C-O activation is similar to other carbonylations of ethers/alcohols: a) V. Mahadevan, Y. D. Y. L. Getzler, G. W. Coates, Angew. Chem. 2002, 114, 2905-2908;
  • 14
    • 0037008572 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 2781-2784;
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 2781-2784
  • 21
    • 53549111705 scopus 로고    scopus 로고
    • Cyclic structures similar to 3 have been postulated as intermediates in amidocarbonylation to form amido acid derivatives (reference [1]).
    • Cyclic structures similar to 3 have been postulated as intermediates in amidocarbonylation to form amido acid derivatives (reference [1]).
  • 23
    • 53549107296 scopus 로고    scopus 로고
    • These substrates can undergo carbonylation under pressing conditions (120°C, 80 bar CO, 41% yield), similar to reference [3], however, these conditions do not provide access to the cycloaddition (vide infra).
    • These substrates can undergo carbonylation under pressing conditions (120°C, 80 bar CO, 41% yield), similar to reference [3], however, these conditions do not provide access to the cycloaddition (vide infra).
  • 24
    • 53549127371 scopus 로고    scopus 로고
    • In addition to commercial, Pd(allyl)Cl}2, pre-synthesized catalyst 6 is slightly more effective Table 1, entry 8, For synthesis of 6, see reference [4
    • 2], pre-synthesized catalyst 6 is slightly more effective (Table 1, entry 8). For synthesis of 6, see reference [4].
  • 25
    • 1542377701 scopus 로고    scopus 로고
    • Examples of chelation assisted C-O oxidative addition: a F. Kakiuchi, M. Usui, S. Ueno, N. Chatani, S. Murai, J. Am. Chem. Soc. 2004, 126, 2706-2707;
    • Examples of chelation assisted C-O oxidative addition: a) F. Kakiuchi, M. Usui, S. Ueno, N. Chatani, S. Murai, J. Am. Chem. Soc. 2004, 126, 2706-2707;
  • 28
    • 53549091949 scopus 로고    scopus 로고
    • This may result from the acidic catalyst in these reactions, inhibiting 3 formation, or the more nucleophilic ROH, which could rapidly trap 3
    • This may result from the acidic catalyst in these reactions, inhibiting 3 formation, or the more nucleophilic ROH, which could rapidly trap 3.
  • 29
    • 22744450570 scopus 로고    scopus 로고
    • For recent representative examples of catalytic pyrrole syntheses: a
    • For recent representative examples of catalytic pyrrole syntheses: a) G. Balme, Angew. Chem. 2004, 116, 6396-6399;
    • (2004) Angew. Chem , vol.116 , pp. 6396-6399
    • Balme, G.1
  • 30
    • 11144250168 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 6238-6241;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 6238-6241


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.