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Palladium-catalyzed Synthesis Of Arylamines From Aryl Halides. Mechanistic Studies Lead To Coupling In The Absence Of Tin Reagents

J. Louie, J. Hartwig
Published 1995 · Chemistry

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Abstract The reaction of aryl halides with secondary amines in the presence of silylamide base and tri- o -tolyphopshine palladium complexes gives arylamine products. This process provides a convenient method for performing these hetero-cross coupling reactions without the necessity for forming tin amides and disposing of tin halides. This reaction follows from a mechanistic analysis of the coupling reaction with tin amides and occurs as a result of the cleavage of palladium aryl halide dimers with secondary amines.
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This paper is referenced by
10.1016/S1460-1567(07)80053-5
Chapter 4 Pyridines
P. Galatsis (2007)
10.1002/anie.200705209
Palladium-catalyzed three-component approach to promazine with formation of one carbon-sulfur and two carbon-nitrogen bonds.
T. Dahl (2008)
10.5012/BKCS.2010.31.12.3848
Mechanistic Study on Reaction of Dichlorophenylphosphine with Dicyclohexylamine
In-Hye Lee (2010)
10.1021/ol2007988
Generation and spectroscopic profiles of stable multiarylaminium radical cations bridged by fluorenes.
Chao-Che Chang (2011)
10.1016/B978-0-12-396532-5.00003-2
Benzotriazole and Its Derivatives as Ligands in Coupling Reaction
Akhilesh K Verma (2012)
10.1007/978-3-642-39016-6_11
A Discussion Between Carbonylation, Noncarbonylation and Decarbonylation
Matthias Beller (2013)
10.1002/CIUZ.201500705
Palladiumkatalyse im industriellen Einsatz
Bjoern Schlummer (2016)
10.1039/c6cp02870e
Blue-shifted emission and enhanced quantum efficiency viaπ-bridge elongation in carbazole-carborane dyads.
Z. Wang (2016)
10.1016/J.COMPTC.2018.04.019
Theoretical investigations on copper catalyzed CN cross-coupling reaction between aryl chlorides and amines
Khalil Ahmad (2018)
10.1021/OM300725F
[Pd(IPr*)(3-Cl-pyridinyl)Cl2]: A Novel and Efficient PEPPSI Precatalyst
Anthony Chartoire (2012)
10.1080/00397911.2014.880789
Palladium-Catalyzed Selective α-Arylation of ortho-Bromoacetophenones
J. V. Jayarama Krishna (2014)
10.1021/OL050130I
Synthesis of N,N-Dialkyl-N'-arylhydrazines via palladium-catalyzed N-arylation by using N,N-dialkylhydrazines/2LiCl adducts.
S. Cacchi (2005)
10.1016/J.MOLCATA.2013.07.011
Synthesis, characterization and catalytic application of some novel binuclear transition metal complexes of bis-(2-acetylthiophene) oxaloyldihydrazone for CN bond formation
D. Singh (2013)
10.1021/OM401028D
N-Heterocyclic Carbene–Palladium(II)–4,5-Dihydrooxazole Complexes: Synthesis and Catalytic Activity toward Amination of Aryl Chlorides
Pei Huang (2014)
10.1039/OC9959200113
Chapter 5. Aromatic compounds
A. Chorlton (1995)
10.1016/S0040-4039(97)10877-2
Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines
S. Jaime-Figueroa (1998)
10.1016/S0022-328X(98)01054-7
Palladium-catalyzed amination of aryl halides and sulfonates
B. Yang (1999)
10.1002/9781119951438.EIBC0263
Organic Synthesis Using Metal-Mediated Coupling Reactions
Felix E. Goodson (2006)
10.1002/anie.200802157
Palladium-catalyzed amination of aryl mesylates.
C. M. So (2008)
10.1016/J.ICA.2010.01.023
Buchwald–Hartwig C–N cross coupling reactions catalyzed by a pseudo-pincer Pd(II) compound
Alcives Avila-Sorrosa (2010)
10.1016/J.TET.2010.06.038
Synthesis of new tetracyclic azaheteroaromatic cores via auto-tandem Pd-catalyzed and one-pot Pd- and Cu-catalyzed double C-N bond formation
Tom R. M. Rauws (2010)
10.1016/J.JORGANCHEM.2012.08.027
Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride
Danielle C. Samblanet (2012)
10.1155/2013/614829
Solid-Phase Organic Synthesis and Catalysis: Some Recent Strategies Using Alumina, Silica, and Polyionic Resins
Basudeb Basu (2013)
10.1039/c4ob00609g
First total syntheses of chrestifoline-B and (±)-chrestifoline-C, and improved synthetic routes to bismurrayafoline-A, bismurrayafolinol and chrestifoline-D.
Carsten Boerger (2014)
10.1039/c5cc03565a
Practical catalytic method for synthesis of sterically hindered anilines.
Melrose Mailig (2015)
10.3762/bjoc.12.156
Catalytic Chan–Lam coupling using a ‘tube-in-tube’ reactor to deliver molecular oxygen as an oxidant
Carl J. Mallia (2016)
10.1002/SLCT.201601552
Copper‐Promoted Direct C‐H Aminationof Benzothiazoles Using Formamides as Nitrogen Sources: An Efficient Approach for Synthesis of 2‐Aminothiazoles
Mengxuan Yu (2016)
10.1021/acs.joc.7b00201
A Method for Identifying and Developing Functional Group Tolerant Catalytic Reactions: Application to the Buchwald-Hartwig Amination.
J. Richardson (2017)
10.1021/OL060349C
Highly efficient synthesis and solid-state characterization of 1,2,4,5-tetrakis(alkyl- and arylamino)benzenes and cyclization to their respective benzobis(imidazolium) salts.
D. M. Khramov (2006)
10.1016/J.TETLET.2007.11.116
An assessment of late transition metals as hydroamination catalysts in the cyclization of C-propargyl vinylogous amides into pyrroles
A. M. Prior (2008)
10.1002/9780470682531.PAT0391
Synthesis of Anilines
J. Hartwig (2009)
10.1016/j.bmcl.2010.03.087
Discovery of anti-inflammatory clinical candidate E6201, inspired from resorcylic lactone LL-Z1640-2, III.
Yongchun Shen (2010)
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