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Volumn 129, Issue 1, 2007, Pages 30-31

Why excess cyanide can be detrimental to Pd-catalyzed cyanation of haloarenes. Facile formation and characterization of [Pd(CN)3(H)] 2 and [Pd(CN)3(Ph)]2-

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; ORGANOHALOGEN DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

EID: 33846044745     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066931d     Document Type: Article
Times cited : (69)

References (26)
  • 2
    • 33846069087 scopus 로고    scopus 로고
    • Pd: Takagi, K.; Okamoto, T.; Sakakibara, Y.; Oka, S. Chem. Lett. 1973, 471.
    • (a) Pd: Takagi, K.; Okamoto, T.; Sakakibara, Y.; Oka, S. Chem. Lett. 1973, 471.
  • 3
    • 0002756370 scopus 로고    scopus 로고
    • Ni: Cassar, L. J. Organomet. Chem. 1973, 54, C57.
    • (b) Ni: Cassar, L. J. Organomet. Chem. 1973, 54, C57.
  • 8
    • 33846051738 scopus 로고    scopus 로고
    • 3, based on C,H-analysis data: Nozaki, K. U.S. Patent 3835123, 1974
    • 3], based on C,H-analysis data: Nozaki, K. U.S. Patent 3835123, 1974.
  • 9
    • 49149138859 scopus 로고    scopus 로고
    • 2- has been reported: Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 208, 273.
    • 2- has been reported: Almeida, J. F.; Pidcock, A. J. Organomet. Chem. 1981, 208, 273.
  • 10
    • 33846034725 scopus 로고    scopus 로고
    • 2·1 was inconclusive because of disorder.
    • 2·1 was inconclusive because of disorder.
  • 11
    • 0001467798 scopus 로고    scopus 로고
    • This stability of 1 is uncommon in the chemistry of palladium hydrides: Grushin, V. V. Chem. Rev. 1996, 96, 2011
    • This stability of 1 is uncommon in the chemistry of palladium hydrides: Grushin, V. V. Chem. Rev. 1996, 96, 2011.
  • 12
    • 37049140602 scopus 로고    scopus 로고
    • 3 in solution: Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
    • 3 in solution: Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
  • 13
    • 33846045014 scopus 로고    scopus 로고
    • The ΔG values (298 K) for the sequential stepwise PPh3 displacement reactions of, Ph3P)4Pd] with cyanide to, Ph3P)3Pd(CN, Ph3P) 2Pd-(CN)2]2, Ph3P)Pd(CN) 3]3, and finally [Pd(CN)4]4- were computed at -52, 23, 112, and +194 kcal mol-1, respectively
    • -1, respectively.
  • 14
    • 0000407644 scopus 로고    scopus 로고
    • For detailed accounts of the pioneering work of Amatore, Jutand, and co-workers in the field, see
    • For detailed accounts of the pioneering work of Amatore, Jutand, and co-workers in the field, see: Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254
    • (1999) J. Organomet. Chem , vol.576 , pp. 254
    • Amatore, C.1    Jutand, A.2
  • 15
    • 0034127063 scopus 로고    scopus 로고
    • and Acc. Chem. Res. 2000, 33, 314.
    • and Acc. Chem. Res. 2000, 33, 314.
  • 16
    • 0038627682 scopus 로고    scopus 로고
    • + as the arylating electrophile: Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
    • + as the arylating electrophile: Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
  • 19
    • 33846057710 scopus 로고    scopus 로고
    • +: Nast, R.; Buelck, J.; Kramolowsky, R. Chem. Ber. 1975, 108, 3461.
    • +: Nast, R.; Buelck, J.; Kramolowsky, R. Chem. Ber. 1975, 108, 3461.
  • 20
    • 33846097550 scopus 로고    scopus 로고
    • 31P NMR (C6H6, 25 °C, δ, 5.5 ppm (s, PPh3, NMR for K2[13CN) 3PdPh] in the D2O phase (25 °C, δ, 1H: 7.1 (t, 1H, p-Ph, 7.2 (t, 2H, m-Ph, 7.5 (d, 2H, o-Ph, 13C: 145.4 (d, JC-C, 7.3 Hz, 2C, mutually trans-CN, 146.7 t, JC-C, 7.3 Hz, 1C, CN trans to Ph
    • C-C = 7.3 Hz, 1C, CN trans to Ph).
  • 21
    • 0032512598 scopus 로고    scopus 로고
    • For instance, cyanide has been used to displace BINAP mono-oxide from its Pd complex: Gladiali, S.; Pulacchini, S.; Fabbri, D.; Manassero, M; Sansoni, M. Tetrahedron: Asymmetry 1998, 9, 391.
    • For instance, cyanide has been used to displace BINAP mono-oxide from its Pd complex: Gladiali, S.; Pulacchini, S.; Fabbri, D.; Manassero, M; Sansoni, M. Tetrahedron: Asymmetry 1998, 9, 391.
  • 22
    • 33846118200 scopus 로고    scopus 로고
    • 2·1 was attempted.
    • 2·1 was attempted.
  • 23
    • 33846116951 scopus 로고    scopus 로고
    • Stirring, Ph3P2Pd(1)Ph] in benzene with D 2O containing a substoichiometric amount (2.9 equiv; see Scheme 2) of K13CN led to extra cyanide-free K2[(13CN) 3PdPh] in the aqueous phase (13C NMR, The separated clear D2O solution turned cloudy in ca. 30 min, and after 12 h, the formation of an amorphous-looking, brown-black precipitate was observed. The mixture was extracted with CD2Cl2 to detect Ph 13CN in the extract (13C NMR, δ: 119.0 (s) and GC-MS
    • 13C NMR, δ: 119.0 (s) and GC-MS).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.