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Volumn 28, Issue 11, 2009, Pages 3288-3302

Phosphinoferrocenyl carboxamides bearing glycine pendant groups: Synthesis, palladium(II) complexes, and catalytic use in polar and aqueous reaction media

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYST; AQUEOUS MIXTURES; AQUEOUS REACTIONS; ARYL BROMIDES; BIS-CHELATE COMPLEXES; CARBOXAMIDES; CLEAVAGE REACTION; CRYSTALLINE FORM; ELECTROCHEMICAL METHODS; ELEMENTAL ANALYSIS; FERROCENE; MULTINUCLEAR NMR; NH GROUPS; PALLADIUM ACETATE; PALLADIUM COMPLEXES; PENDANT GROUPS; PEPTIDE COUPLING; PHENYLBORONIC ACIDS; PHOSPHINE COMPLEX; PHOSPHINE OXIDE; PHOSPHINOFERROCENYL; POLAR SOLVENTS; PURE WATER; SPECTROSCOPIC METHOD; SUZUKI-MIYAURA CROSS-COUPLING;

EID: 66349104207     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900209j     Document Type: Article
Times cited : (54)

References (122)
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    • For examples concerning amidation of ferrocene phosphinocarboxylic acids, see refs 6 and 8
    • For examples concerning amidation of ferrocene phosphinocarboxylic acids, see refs 6 and 8.
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    • Complex 8 is virtually insoluble in all common laboratory solvents except for warm dimethylsulfoxide, in which, however, it rapidly decomposes.
    • Complex 8 is virtually insoluble in all common laboratory solvents except for warm dimethylsulfoxide, in which, however, it rapidly decomposes.
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    • The distances from the Cp(2) plane for 99aare as follows: C(11) 0.109(4)/0.012(4), O(1) 0.034(3)/-0.275(3), and N(1) 0.268(3)/0.295(4) Å.
    • The distances from the Cp(2) plane for 99aare as follows: C(11) 0.109(4)/0.012(4), O(1) 0.034(3)/-0.275(3), and N(1) 0.268(3)/0.295(4) Å.
  • 86
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    • The H-bond parameters are as follows: C(15)-H(15) ⋯ O(92): C(15) ⋯ O(92) ) 3.272(5) Å, angle at H(15) ) 149°; C(20)-H(20) ⋯ Cl: C(20) ⋯ Cl ) 3.673(4) Å; angle at H(20) ) 155°; C(24)-H(24A) ⋯ O(1): C(24) ⋯ O(1) ) 3.384(5) Å, angle at H(24A) ) 144°.
    • The H-bond parameters are as follows: C(15)-H(15) ⋯ O(92): C(15) ⋯ O(92) ) 3.272(5) Å, angle at H(15) ) 149°; C(20)-H(20) ⋯ Cl: C(20) ⋯ Cl ) 3.673(4) Å; angle at H(20) ) 155°; C(24)-H(24A) ⋯ O(1): C(24) ⋯ O(1) ) 3.384(5) Å, angle at H(24A) ) 144°.
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    • 3C-H ⋯ O contacts to carbonyl oxygens of the ligand. The H-bond parameters are as follows: C(80)-H(80) ⋯ O(2): C(80) ⋯ O(2) ) 3.056(6) Å; angle at H(80) ) 163°; C(90)-H(90) ⋯ O(1): C(90) ⋯ O(1) ) 3.111(7) Å; angle at H(90) ) 164°.
    • 3C-H ⋯ O contacts to carbonyl oxygens of the ligand. The H-bond parameters are as follows: C(80)-H(80) ⋯ O(2): C(80) ⋯ O(2) ) 3.056(6) Å; angle at H(80) ) 163°; C(90)-H(90) ⋯ O(1): C(90) ⋯ O(1) ) 3.111(7) Å; angle at H(90) ) 164°.
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    • The molecules of 10 form infinite chains along the b direction via N-H ⋯ Cl contacts between alternating, structurally independent moieties 1 and 2. The H-bond parameters are as follows (without symmetry codes): N(11)-H(1N) ⋯ Cl(2): N(11) ⋯ Cl(2) ) 3.249(3) Å, angle at H(1N) ) 155°; N(21)-H(2N) ⋯ Cl(1): N(21) ⋯ Cl(1) ) 3.194(3) Å, angle at H(2N)) 150°. These chains are interconnected by C-H ⋯ O contacts.
    • The molecules of 10 form infinite chains along the b direction via N-H ⋯ Cl contacts between alternating, structurally independent moieties 1 and 2. The H-bond parameters are as follows (without symmetry codes): N(11)-H(1N) ⋯ Cl(2): N(11) ⋯ Cl(2) ) 3.249(3) Å, angle at H(1N) ) 155°; N(21)-H(2N) ⋯ Cl(1): N(21) ⋯ Cl(1) ) 3.194(3) Å, angle at H(2N)) 150°. These chains are interconnected by C-H ⋯ O contacts.
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    • Structural data for some related compounds can be found in: (a)štěpnička, P.; Císařová, I. Inorg. Chem. 2006, 45, 8785.
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    • The maximum deviations from the least-squares planes comprising the palladium and its four ligating atoms are ca. 0.10/0.14 Å for 10(molecule 1/2), ca. 0.19 Å for 11, and ca. 0.12/0.11 Å for 12(molecule 1/2).
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    • Although any ring puckering analysis for the palladacycles can be regarded as dubious due to very different in-ring bond lengths, the parameters describe the same moiety and their trend is unambiguous. For a reference, see: Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354.
  • 98
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    • The distances of the C/O/N atoms forming the amide plane from the Cp(2) plane are as follows (in Å): 10: 0.054(4)/0.093(3)/0.047(3) and [0.021(4)/0.063(3)/0.027(3)] for molecule 1 [molecule 2]; 11: 0.241(2)/ 0.665(1)/0.025(2); 12: 0.119(2)/0.278(2)/0.657(2) [0.271(2)/0.125(2)/0. 751(2)] for molecule 1 [molecule 2]. Directions of the displacement are not indicated.
    • The distances of the C/O/N atoms forming the amide plane from the Cp(2) plane are as follows (in Å): 10: 0.054(4)/0.093(3)/0.047(3) and [0.021(4)/0.063(3)/0.027(3)] for molecule 1 [molecule 2]; 11: 0.241(2)/ 0.665(1)/0.025(2); 12: 0.119(2)/0.278(2)/0.657(2) [0.271(2)/0.125(2)/0. 751(2)] for molecule 1 [molecule 2]. Directions of the displacement are not indicated.
  • 99
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    • The compounds do not undergo defined reductions (ill-defined or none at all) in the potential window provided by the solvent and, therefore, were studied mainly in the anodic region
    • The compounds do not undergo defined reductions (ill-defined or none at all) in the potential window provided by the solvent and, therefore, were studied mainly in the anodic region.
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    • pc.
    • pc.
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    • An additional oxidative peak is observed for 4 E pa ̃ 1.0 V, probably due to amide oxidation
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    • 2/5, 24 h).
    • 2/5, 24 h).
  • 121


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.