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Volumn 12, Issue 7, 2010, Pages 1476-1479

Synthesis of 2-indolylphosphines by palladium-catalyzed annulation of 1-alkynylphosphine sulfides with 2-iodoanilines

Author keywords

[No Author keywords available]

Indexed keywords

2 INDOLYLPHOSPHINE; 2-INDOLYLPHOSPHINE; ALKYNE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM; PHOSPHINE DERIVATIVE; SULFIDE;

EID: 77950291399     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1001544     Document Type: Article
Times cited : (38)

References (62)
  • 1
    • 20544450502 scopus 로고    scopus 로고
    • 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany
    • (a) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
  • 23
    • 34547489616 scopus 로고    scopus 로고
    • Syntheses of arylphosphines by diels-alder reactions of 1-alkynylphosphine oxides were reported
    • Syntheses of arylphosphines by Diels-Alder reactions of 1-alkynylphosphine oxides were reported: (a) Ashburn, B. O.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2007, 129, 9109-9116.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9109-9116
    • Ashburn, B.O.1    Carter, R.G.2    Zakharov, L.N.3
  • 26
    • 0000428035 scopus 로고
    • The palladium-catalyzed annulation of alkynes with 2-iodoanilines
    • The palladium-catalyzed annulation of alkynes with 2-iodoanilines was reported by Larock and others: (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6689-6690
    • Larock, R.C.1    Yum, E.K.2
  • 53
    • 77950271099 scopus 로고    scopus 로고
    • The structure of 3aa was confirmed by X-ray crystallographic analysis. See the Supporting Information.
    • The structure of 3aa was confirmed by X-ray crystallographic analysis. See the Supporting Information.
  • 54
    • 77950286402 scopus 로고    scopus 로고
    • The reaction of 1.2 equiv of 2a gave 3aa in 61% NMR yield. The concentration of 2a would affect the efficiency of the reaction.
    • The reaction of 1.2 equiv of 2a gave 3aa in 61% NMR yield. The concentration of 2a would affect the efficiency of the reaction.
  • 55
    • 77950268024 scopus 로고    scopus 로고
    • See the Supporting Information.
    • See the Supporting Information.
  • 56
    • 77950277894 scopus 로고    scopus 로고
    • 2 gave the best result is not clear at this stage. The ligand on palladium precursors would affect the catalytic activity. Pd(II) precursors would be reduced to Pd(0) complexes under the reaction conditions, which would participate in the catalytic cycle.
    • 2 gave the best result is not clear at this stage. The ligand on palladium precursors would affect the catalytic activity. Pd(II) precursors would be reduced to Pd(0) complexes under the reaction conditions, which would participate in the catalytic cycle.
  • 57
    • 77950229375 scopus 로고    scopus 로고
    • A significant amount of phosphine sulfide derived from an additional phosphine ligand was observed after the reaction.
    • A significant amount of phosphine sulfide derived from an additional phosphine ligand was observed after the reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.