Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines

Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines

A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ε-C(sp2)−H bonds of γ-arylpropylamine substrates is reported. This reaction proceeds selectively with a variety of γ-arylpropylamines bearing strongly electron-donating or withdrawing substituents, complementing our pr...

Full description

Bibliographic Details
Main Authors:	William A. Nack, Xinmou Wang, Bo Wang, Gang He, Gong Chen
Format:	Article
Language:	English
Published:	Beilstein-Institut 2016-06-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	iodination palladium remote C–H activation tetrahydroquinoline
Online Access:	https://doi.org/10.3762/bjoc.12.119

Similar Items

Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization
by: Ryan Pearson, et al.
Published: (2013-05-01)

Hypervalent Iodine Reagents in Palladium-Catalyzed Oxidative Cross-Coupling Reactions
by: Samata E. Shetgaonkar, et al.
Published: (2020-09-01)

Synthesis of Novel <i>Spiro</i>-Tetrahydroquinoline Derivatives and Evaluation of Their Pharmacological Effects on Wound Healing
by: Yan-Cheng Liou, et al.
Published: (2021-06-01)

Facile synthesis and in vitro anticancer evaluation of a new series of tetrahydroquinoline
by: Usama Fathy, et al.
Published: (2021-10-01)

Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
by: P. S. Pradeep, et al.
Published: (2014-09-01)

Experimental and Theoretical Approaches in the Study of Phenanthroline‐Tetrahydroquinolines for Alzheimer's Disease
by: Dr. Yorley Duarte, et al.
Published: (2019-05-01)

Crystal structure of 1-methanesulfonyl-1,2,3,4-tetrahydroquinoline
by: S. Jeyaseelan, et al.
Published: (2015-01-01)

An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis
by: Hana Doušová, et al.
Published: (2015-05-01)

Crystal structure of cis-1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one
by: P. S. Pradeep, et al.
Published: (2014-09-01)

Crystal structure of 1-benzylsulfonyl-1,2,3,4-tetrahydroquinoline
by: S. Jeyaseelan, et al.
Published: (2015-04-01)

(2<i>S*</i>,4<i>S*</i>)-4-[(<i>E</i>)-(2,2-Dimethylhydrazono)methyl]-6-methoxy-4-methyl-2-[(<i>E</i>)-styryl]-1,2,3,4-tetrahydroquinoline
by: José Clerigué, et al.
Published: (2021-06-01)

Biological Properties of New Chiral 2-Methyl-5,6,7,8-tetrahydroquinolin-8-amine-based Compounds
by: Giorgio Facchetti, et al.
Published: (2020-11-01)

Efficient synthesis and antioxidant activity of novel N-propargyl tetrahydroquinoline derivatives through the cationic Povarov reaction
by: Yeray A. Rodriguez Núñez, et al.
Published: (2019-08-01)

On the ortho - para enhancement of molecular iodine by selective laser excitation
by: Booth, James L.
Published: (2010)

Novel 4-ferrocenyl-8-(phenylthio)-1,2,3,4-tetrahydroquinoline: Design, synthesis and spectral characterization
by: Minić Aleksandra, et al.
Published: (2019-01-01)

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes
by: Jing Sun, et al.
Published: (2012-10-01)

The Role of the Conjugate Bridge in Electronic Structures and Related Properties of Tetrahydroquinoline for Dye Sensitized Solar Cells
by: You-Zhi Wu, et al.
Published: (2013-03-01)

Synthesis of novel tetrahydroquinoline derivatives from α,α′-bis(substituted-benzylidene)cycloalkanones
by: Enayatollah Sheikhhosseini, et al.
Published: (2016-09-01)

Crystal structure of 1-[(6-chloropyridin-3-yl)sulfonyl]-1,2,3,4-tetrahydroquinoline
by: S. Jeyaseelan, et al.
Published: (2015-06-01)

Mechanochemical Aza-Vinylogous Povarov Reactions for the Synthesis of Highly Functionalized 1,2,3,4-Tetrahydroquinolines and 1,2,3,4-Tetrahydro-1,5-Naphthyridines
by: José Clerigué, et al.
Published: (2021-03-01)

Modifications on the Tetrahydroquinoline Scaffold Targeting a Phenylalanine Cluster on GPER as Antiproliferative Compounds against Renal, Liver and Pancreatic Cancer Cells
by: David Méndez-Luna, et al.
Published: (2021-01-01)

Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp2 C–H bond activation in ball mills
by: Zi Liu, et al.
Published: (2018-02-01)

Protective Effect of Tetrahydroquinolines from the Edible Insect <i>Allomyrina dichotoma </i>on LPS-Induced Vascular Inflammatory Responses
by: InWha Park, et al.
Published: (2020-05-01)

The green synthesis of N-hydroxyethyl-substituted 1,2,3,4-tetrahydroquinolines with acidic ionic liquid as catalyst
by: Guo Hui, et al.
Published: (2020-10-01)

One-Pot Multicomponent Synthesis and Bioevaluation of Tetrahydroquinoline Derivatives as Potential Antioxidants, α-Amylase Enzyme Inhibitors, Anti-Cancerous and Anti-Inflammatory Agents
by: Samra Farooq, et al.
Published: (2020-06-01)

Palladium-Catalyzed Synthesis and Transformation of Organoboranes
by: Sebelius, Sara
Published: (2006)

Synthesis and Crystal Structure of Two Nitro-Regioisomers of cis-4(4- Methoxyphenyl)-3-Methyl-2-Phenyl-1,2,3,4-Tetrahydroquinoline
by: Arnold R. Romero Bohórquez, et al.
Published: (2013-04-01)

A New Palladium-Catalyzed Phenyl-Alkene Bond Formation
by: RenÃƒÂ© Roy, et al.
Published: (2002-05-01)

Flavouring Group Evaluation 34: One tetrahydroquinoline derivative from chemical group 28 ‐ Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
by: European Food Safety Authority (EFSA)
Published: (2008-08-01)

Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans
by: Verónica Guilarte, et al.
Published: (2011-09-01)

Palladium/Heteropoly Acid Catalyzed Oxidative Coupling of 2-Methoxy-1,4-benzoquinone with Arenes
by: Oliveira Rosilene A. de, et al.
Published: (2002-01-01)

Bisindole [3]arenes-Indolyl Macrocyclic Arenes Having Significant Iodine Capture Capacity
by: Su, D., et al.
Published: (2022)

1,7-Sigmatropic rearrangement in 1,2-dihydro and 1,2,3,4-tetrahydroquinoline synthesis using marine sponge/H2C2O4 as a catalyst
by: Mohammad Reza Shushizadeh, et al.
Published: (2015-11-01)

Theoretical aspects of palladium-catalyzed direct arylations of heterocycles
by: Blignaut, Jacques Philip
Published: (2018)

Suppression of Pax3–MITF-M Axis Protects from UVB-Induced Skin Pigmentation by Tetrahydroquinoline Carboxamide
by: Yong-Pyo Choi, et al.
Published: (2020-12-01)

Advances in Palladium-Catalyzed Conjunctive Cross-Coupling:
by: Wilhelmsen, Christopher Alexander
Published: (2021)

Palladium(II) Catalyzed Cyclization-Carbonylation-Cyclization Coupling Reaction of (ortho-Alkynyl Phenyl) (Methoxymethyl) Sulfides Using Molecular Oxygen as the Terminal Oxidant
by: Rong Shen, et al.
Published: (2016-09-01)

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines
by: David R. Chisholm, et al.
Published: (2016-08-01)

Palladium-Catalyzed Amide Formation via Masked Isocyanates
by: Brzezinski, David
Published: (2020)

Palladium-Catalyzed Synthesis and Transformation of Organoboranes
by: Sebelius, Sara
Published: (2006)