Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes

Journal of the American Chemical Society

Volumn 128, Issue 11, 2006, Pages 3584-3591

  Shekhar, Shashank ^a   Ryberg, Per ^a   Hartwig, John F ^a   Mathew, Jinu S ^b   Blackmond, Donna G ^b   Strieter, Eric R ^c   Buchwald, Stephen L ^c  

^a YALE UNIVERSITY   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CATALYSIS; DECOMPOSITION; ENZYME KINETICS; MATHEMATICAL TRANSFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS;

ARYLAMINE; CATALYTIC REACTION; DIPHENYLPHOSPHINE; PALLADIUM COMPLEXES;

HALOGEN COMPOUNDS;

1,1 BINAPHTHALENE 2,2' DIYLBIS(DIPHENYLPHOSPHINE); AMINE; BROMOBENZENE; HALIDE; NAPHTHALENE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); DISSOCIATION; ELIMINATION REACTION; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY;

AMINATION; AMINES; BENZENE DERIVATIVES; CATALYSIS; HYDROCARBONS, HALOGENATED; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 33645387715     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045533c     Document Type: Article

References (13)

1. Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E. I., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, p 1051.
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7. The reaction of free dba with NaOtBu and either the primary or secondary amine rapidly consumes dba at room temperature and generates several products.
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9. Data obtained in 2002 and in 2005 from MIT and Imperial College agree within 5%.
10. 3/BINAP, a lack of overlay between the two curves could have confirmed that catalyst deactivation, rather than positive order kinetics in [secondary amine], accounted for the rate profiles observed in Figure 1b of ref 5.
11. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302.
12. 2] in the presence and in the absence of amine: Shekhar, S.; Ryberg, P.; Hartwig, J. F. Org. Lett. 2006, 8, 851.
13. Cornish-Bowden, A. In Fundamentals of Enzyme Kinetics: Portland Press: London, 1995; p 88.