☆ 4.8 Article

Novel N(SCF3)(CF3)-amines: synthesis, scalability and stability

CHEMICAL SCIENCE (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

General Synthesis of N-Trifluoromethyl Compounds with N-Trifluoromethyl Hydroxylamine Reagents

Shuai Liu et al.

Summary: This study reports a method for the design and synthesis of novel N-Cbz- and N-Boc-N-trifluoromethyl hydroxylamine reagents using silver-mediated oxidative trifluoromethylation. These reagents have been successfully applied to incorporate a NCF3 moiety into commonly used unsaturated substrates, enabling efficient and regioselective C-H trifluoromethylamination. Additionally, a variety of substrates can undergo tandem trifluoromethylamination/functionalization to deliver structurally diverse N-trifluoromethyl aliphatic and heteroaromatic amines.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Metal-Free SF6 Activation: A New SF5-Based Reagent Enables Deoxyfluorination and Pentafluorosulfanylation Reactions

Alexis Taponard et al.

Summary: The activation of SF6 under metal-free and visible light conditions was investigated and a new fluorinating reagent was synthesized. This reagent was efficient in the deoxyfluorination of CO2 and fluorinative desulfurization of CS2 to produce useful fluorinated amines. Additionally, the reagent was able to generate Cl-SF5 gas, which was used for the chloro-pentafluorosulfanylation of alkynes and alkenes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Access to CyclicN-Trifluoromethyl Ureas through PhotocatalyticActivation of Carbamoyl Azides

Samir Bouayad-Gervais et al.

Summary: In this study, we reported a strategy for the mild activation of carbamoyl azides using a blue light/[Ir] catalyst, which provides access to N-trifluoromethylimidazolidinones and benzimidazolones with high stereoselectivity. Our combined computational and experimental studies suggest an electron rebound mechanism initiated by reduction-triggered nitrogen loss, followed by oxidation and subsequent C-H insertion.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Stable and Storable N(CF3)2 Transfer Reagents

Leon N. Schneider et al.

Summary: Fluorinated groups are crucial for drug design, agrochemicals, and materials science, with the N(CF3)2 group being rare in compounds. This study presents a series of Cu-I and Ag-I bis(trifluoromethyl)amido complexes stabilized by N- and P-donor ligands, showing unprecedented stability and potential applications.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Add to Collection

Editorial Material Chemistry, Medicinal

The powerful symbiosis between synthetic and medicinal chemistry

Stefan Schiesser et al.

FUTURE MEDICINAL CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Thiocarbamoyl Fluoride Synthesis by Deconstructive Diversification of Arylated Tetrahydroisoquinolines

Wentao Xu et al.

Summary: Deconstructive functionalization of cyclic amines provides access to chemicals with diverse skeletons. Tertiary amines are converted to thiocarbamoyl fluorides using photoredox catalysis, enabling the synthesis of trifluoromethylamines from AgF in a one-pot method. The synthesized thiocarbamoyl fluorides can be further converted into esters.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of N-CF3 Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF3 Carbamoyl Fluorides

Christian D. -T. Nielsen et al.

Summary: The study reported a synthetic method for N-trifluoromethyl alkynamides and found that this synthetic compound can serve as a platform to unlock access to other valuable derivatives.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of N-trifluoromethyl amides from carboxylic acids

Jianbo Liu et al.

Summary: The synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature has been reported. This method desulfurizes isothiocyanates with AgF and then acylates the formed derivative to afford N-trifluoromethyl amides, including previously inaccessible structures. The strategy provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners and could find application in the modification of advanced intermediates.

CHEM (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of N-CF3 hydrazines through radical trifluoromethylation of azodicarboxylates

Tingting Cao et al.

Summary: We report the synthesis of a novel family of N-CF3 hydrazines using the available and cheap Langlois reagent. These derivatives exhibit very high stability under different conditions and are excellent precursors for building previously inaccessible N-CF3 functionalized compounds.

CHEMICAL COMMUNICATIONS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

N-Trifluoromethyl Hydrazines, Indoles and Their Derivatives

Samir Bouayad-Gervais et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Add to Collection

Review Chemistry, Multidisciplinary

Contribution of Organofluorine Compounds to Pharmaceuticals

Munenori Inoue et al.

ACS OMEGA (2020)

Add to Collection

Article Multidisciplinary Sciences

Current Contributions of Organofluorine Compounds to the Agrochemical Industry

Yuta Ogawa et al.

ISCIENCE (2020)

Add to Collection

Article Chemistry, Medicinal

N-Trifluoromethyl Amines and Azoles: An Underexplored Functional Group in the Medicinal Chemist's Toolbox

Stefan Schiesser et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

Add to Collection

Article Chemistry, Organic

Direct Synthesis of Thiocarbamoyl Fluorides and Trifluoromethylamines Through Fluorinative Desulfurization

Killian Onida et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Add to Collection

Article Multidisciplinary Sciences

Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas

Thomas Scattolin et al.

NATURE (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Direct Synthesis of Carbamoyl Fluorides by CO2 Deoxyfluorination

Killian Onida et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Article Chemistry, Multidisciplinary

One-pot synthesis of trifluoromethyl amines and perfluoroalkyl amines with CF3SO2Na and RfSO2Na

Shuaishuai Liang et al.

CHEMICAL COMMUNICATIONS (2019)

Add to Collection

Review Chemistry, Multidisciplinary

The main and recent syntheses of the N-CF3 motif

Thierry Milcent et al.

COMPTES RENDUS CHIMIE (2018)

Add to Collection

Article Chemistry, Medicinal

Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design

Nicholas A. Meanwell

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me4N)SCF3

Thomas Scattolin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection

Article Chemistry, Organic

N-Trifluoromethylation of Nitrosoarenes with Sodium Triflinate

Angela van der Werf et al.

ORGANIC LETTERS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines

Jiao Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Investigating the Influence of (Deoxy) fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method

Bruno Linclau et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Triphenylphosphine-Mediated Deoxygenative Reduction of CF3SO2Na and Its Application for Trifluoromethylthiolation of Aryl Iodides

Yi Yang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Add to Collection

Article Chemistry, Organic

Quantitative Scale for the Trifluoromethylthio Cation-Donating Ability of Electrophilic Trifluoromethylthiolating Reagents

Man Li et al.

ORGANIC LETTERS (2016)

Add to Collection

Article Chemistry, Organic

New entries toward the synthesis of OCF3-containing molecules

Tatiana Besset et al.

ORGANIC CHEMISTRY FRONTIERS (2016)

Add to Collection

Article Chemistry, Medicinal

Applications of Fluorine in Medicinal Chemistry

Eric P. Gillis et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Add to Collection

Review Chemistry, Multidisciplinary

Synthetic Methods for Compounds Having CF3-S Units on Carbon by Trifluoromethylation, Trifluoromethylthiolation, Triflylation, and Related Reactions

Xiu-Hua Xu et al.

CHEMICAL REVIEWS (2015)

Add to Collection

Article Chemistry, Multidisciplinary

N-Trifluoromethylthiosaccharin: An Easily Accessible, Shelf-Stable, Broadly Applicable Trifluoromethylthiolating Reagent

Chunfa Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Add to Collection

Article Chemistry, Medicinal

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals

Edon Vitaku et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

Add to Collection

Article Chemistry, Multidisciplinary

N-Trifluoromethylthiophthalimide: A Stable Electrophilic SCF3-Reagent and its Application in the Catalytic Asymmetric Trifluoromethylsulfenylation

Teerawut Bootwicha et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Add to Collection

Article Chemistry, Multidisciplinary

Direct Electrophilic N-Trifluoromethylation of Azoles by a Hypervalent Iodine Reagent

Katrin Niedermann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Add to Collection

Article Chemistry, Multidisciplinary

A Ritter-Type Reaction: Direct Electrophilic Trifluoromethylation at Nitrogen Atoms Using Hypervalent Iodine Reagents

Katrin Niedermann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Add to Collection

Review Chemistry, Multidisciplinary

Understanding organofluorine chemistry. An introduction to the C-F bond

David O'Hagan

CHEMICAL SOCIETY REVIEWS (2008)

Add to Collection

Article Chemistry, Organic

CF3 oxonium salts, O-(trifluoromethyl)dibenzofuranium salts:: In situ synthesis, properties, and application as a real CF3+ species Reagent

Teruo Umemoto et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

Add to Collection

Article Chemistry, Organic

Trifluoromethylsulfenylation of masked carbonyl compounds

S Munavalli et al.

SYNTHETIC COMMUNICATIONS (2000)

Add to Collection

© Peeref 2019-2024. All rights reserved.