4.8 Article

3-Position-Selective C-H Trifluoromethylation of Pyridine Rings Based on Nucleophilic Activation br

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Borane-Catalyzed C3-Alkylation of Pyridines with Imines,Aldehydes, or Ketones as Electrophiles

Zhong Liu et al.

Summary: This study reports a borane-catalyzed tandem reaction method that achieves exclusively C3-selective alkylation of pyridines, providing a practical tool for late-stage functionalization of structurally complex pharmaceuticals bearing a pyridine moiety.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

C3-Selective Trifluoromethylthiolation and Difluoromethylthiolation of Pyridines and Pyridine Drugs via Dihydropyridine Intermediates

Xin-Yue Zhou et al.

Summary: In this study, a method for functionalization of pyridines was reported, which exhibits high selectivity towards trifluoromethylthio and difluoromethylthio groups. The method can be used for late-stage functionalization of pyridine drugs, resulting in the generation of new drug candidates.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Review Chemistry, Multidisciplinary

Regioselective C-H Trifluoromethylation of Heteroaromatic Compounds

Yoichiro Kuninobu et al.

Summary: This review article focuses on strategies for regioselective C-H trifluoromethylation of heteroaromatic compounds, categorized into five sections discussing different ring-sized heteroaromatic compounds and reaction sites.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2021)

Article Multidisciplinary Sciences

Phosphorus-mediated sp2-sp3 couplings for C-H fluoroalkylation of azines

Xuan Zhang et al.

Summary: Fluoroalkyl groups have significant effects on the physical properties of pharmaceuticals and impact various metrics related to their pharmacokinetics and pharmacodynamics. The development of new fluoroalkylation reactions has led to the direct conversion of C-H bonds into complex C-CF2X groups in drug-like molecules. A novel approach using bench-stable fluoroalkylphosphines allows for the selective conversion of C-H bonds in pyridine building blocks and pharmaceuticals without the need for preinstalled functional groups or directing groups.

NATURE (2021)

Article Chemistry, Multidisciplinary

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

Jin Choi et al.

Summary: This study presents a simple maleate-derived blocking group for the direct position-selective C-4 alkylation of pyridines, allowing for exquisite control and inexpensive access to valuable building blocks. The method is operationally simple and scalable, applied to access known structures rapidly and inexpensively, and signifies an interesting strategic departure in the use of Minisci chemistry.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

C2-Selective silylation of pyridines by a rhodium-aluminum complex

Naofumi Hara et al.

Summary: A C2-selective mono-silylation of various pyridines has been developed using a Rh-Al complex, where the site- and mono-selectivity are controlled by the coordination of pyridine to the Lewis-acidic Al center. A reaction mechanism is proposed based on the isolation of a (2-pyridyl)silylrhodium intermediate from several mechanistic studies.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Organic

Regioselective Direct C-H Trifluoromethylation of Pyridine

Xiao Yang et al.

ORGANIC LETTERS (2020)

Article Chemistry, Multidisciplinary

Nickel(IV)-Catalyzed C-H Trifluoromethylation of (Hetero)arenes

Elizabeth A. Meucci et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent

Yao Ouyang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Aleksei Yevgen'evich Chichibabin (1871-1945): A Century of Pyridine Chemistry

David E. Lewis

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

C-H Functionalization of Azines

Kei Murakami et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds

Masahiro Nagase et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Selective Functionalization of Pyridines via Heterocyclic Phosphonium Salts

Michael C. Hilton et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction

Lu Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp3 C-Si Bonds

Narasimhulu Gandhamsetty et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Multidisciplinary Sciences

A scalable and operationally simple radical trifluoromethylation

Joel W. Beatty et al.

NATURE COMMUNICATIONS (2015)

Article Chemistry, Multidisciplinary

Exceedingly Fast Copper(II)-Promoted ortho C-H Trifluoromethylation of Arenes using TMSCF3

Ming Shang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Trifluoromethylation of arenediazonium salts with fluoroform-derived CuCF3 in aqueous media

Anton Lishchynskyi et al.

CHEMICAL COMMUNICATIONS (2014)

Article Multidisciplinary Sciences

Regioselective trifluoromethylation of N-heteroaromatic compounds using trifluoromethyldifluoroborane activator

Tomoaki Nishida et al.

NATURE COMMUNICATIONS (2014)

Article Chemistry, Multidisciplinary

Copper-mediated trifluoromethylation of aryl-, heteroaryl-, and vinyltrifluoroborates with Langlois' reagent

Srinivas Reddy Dubbaka et al.

RSC ADVANCES (2014)

Article Chemistry, Multidisciplinary

Silver-Mediated Trifluoromethylation of Aryldiazonium Salts: Conversion of Amino Group into Trifluoromethyl Group

Xi Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Multidisciplinary Sciences

Practical and innate carbon-hydrogen functionalization of heterocycles

Yuta Fujiwara et al.

NATURE (2012)

Article Chemistry, Multidisciplinary

A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides

Hiroyuki Morimoto et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Copper-mediated trifluoromethylation of arylboronic acids by trifluoromethyl sulfonium salts

Cheng-Pan Zhang et al.

CHEMICAL COMMUNICATIONS (2011)

Article Multidisciplinary Sciences

Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis

David A. Nagib et al.

NATURE (2011)

Article Multidisciplinary Sciences

Innate C-H trifluoromethylation of heterocycles

Yining Ji et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2011)

Article Chemistry, Inorganic & Nuclear

Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents

Matthias S. Wiehn et al.

JOURNAL OF FLUORINE CHEMISTRY (2010)

Article Chemistry, Multidisciplinary

Selective C-4 Alkylation of Pyridine by Nickel/Lewis Acid Catalysis

Yoshiaki Nakao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Aromatic trifluoromethylation catalytic in copper

Masahiro Oishi et al.

CHEMICAL COMMUNICATIONS (2009)

Article Chemistry, Multidisciplinary

A strategy for C-H activation of pyridines: Direct C-2 selective alkenylation of pyridines by Nickel/Lewis acid catalysis

Yoshiaki Nakao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Organic

Regiospecific synthesis of 4-(2-oxoalkyl)pyridines

AR Katritzky et al.

ORGANIC LETTERS (2001)