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Volumn 10, Issue 23, 2008, Pages 5325-5328

Insights into palladium-catalyzed cyanation of bromobenzene: Additive effects on the rate-limiting step

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; BROMOBENZENE; CYANIDE; NITRILE; ORGANOMETALLIC COMPOUND; PALLADIUM; WATER; ZINC BROMIDE; ZINC DERIVATIVE;

EID: 61349197514     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8016935     Document Type: Article
Times cited : (109)

References (38)
  • 20
    • 33749515284 scopus 로고    scopus 로고
    • (a) Seki, M. Synthesis 2006, 18, 2975-2992.
    • (2006) Synthesis , vol.18 , pp. 2975-2992
    • Seki, M.1
  • 28
    • 61349109951 scopus 로고    scopus 로고
    • (s)/mL).
    • (s)/mL).
  • 29
    • 61349193055 scopus 로고    scopus 로고
    • In the absence of Zn powder, the reaction stalled at low conversion as observed in refs 8 and 10a. We believe that the zinc dust should play a role to maintain palladium(0) complexes, avoiding inhibition processes of the catalyst system
    • In the absence of Zn powder, the reaction stalled at low conversion as observed in refs 8 and 10a. We believe that the zinc dust should play a role to maintain palladium(0) complexes, avoiding inhibition processes of the catalyst system.
  • 30
    • 61349101693 scopus 로고    scopus 로고
    • Reproducibility of the reaction heat flow profile versus time has been checked, and the heat of reaction was in average 26.8 (±1.5) kcal/mol
    • Reproducibility of the reaction heat flow profile versus time has been checked, and the heat of reaction was in average 26.8 (±1.5) kcal/mol.
  • 31
    • 33645387715 scopus 로고    scopus 로고
    • A significant induction period could be attributed to the slow activation of the catalytic precursors. A solution of Pd2(dba) 3/dppf/Zn was stirred for 20 min at rt before addition of Zn(CN) 2 and the reaction solution was equilibrated at 95°C for 45 min; no significant difference in the heat flow profile was observed with longer equilibration time 1 h, For palladium complexes activation, see: Shekhar, S, Ryberg, P, Hartwig, J. F, Mathew, J. S, Blackmond, D. G, Stricter, E. R, Buchwald, S. J. Am. Chem. Soc. 2006, 128, 3584-3591
    • 2 and the reaction solution was equilibrated at 95°C for 45 min; no significant difference in the heat flow profile was observed with longer equilibration time (1 h). For palladium complexes activation, see: Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Stricter, E. R.; Buchwald, S. J. Am. Chem. Soc. 2006, 128, 3584-3591.
  • 32
    • 61349121261 scopus 로고    scopus 로고
    • The order observed at high palladium concentration would support the presence of an inactive palladium dimer. The authors would like to acknowledge one of the referees for their comments and suggestions on the interpretation of the catalyst order
    • The order observed at high palladium concentration would support the presence of an inactive palladium dimer. The authors would like to acknowledge one of the referees for their comments and suggestions on the interpretation of the catalyst order.
  • 33
    • 61349184266 scopus 로고    scopus 로고
    • Another possible role of zinc bromide, mentioned by one of the referees, is that it could presumably act as Lewis acid, facilitating halide abstraction from an oxidative addition intermediate
    • Another possible role of zinc bromide, mentioned by one of the referees, is that it could presumably act as Lewis acid, facilitating halide abstraction from an oxidative addition intermediate.
  • 34
    • 61349136152 scopus 로고    scopus 로고
    • -] = 0.007 M).
    • -] = 0.007 M).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.