Recent Progress on Methods for the Preparation of Mono/Di/Trifluoromethoxylation Reagents DOI
Wei Zheng,

Fengzheng Liu,

Hongqiong Zhao

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(11), P. 3321 - 3321

Published: Jan. 1, 2024

Language: Английский

Review and Theoretical Analysis of Fluorinated Radicals in Direct CAr−H Functionalization of (Hetero)arenes DOI Creative Commons
Anthony J. Fernandes, Rahul Giri, K. N. Houk

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(16)

Published: Jan. 29, 2024

Abstract We highlight key contributions in the field of direct radical C Ar − H (hetero)aromatic functionalization involving fluorinated radicals. A compilation Functional Group Transfer Reagents and their diverse activation mechanisms leading to release radicals are discussed. The substrate scope for each is analyzed classified into three categories according electronic properties substrates. Density functional theory computational analysis provides insights chemical reactivity several through electrophilicity nucleophilicity parameters. Theoretical reduction potentials also highlights remarkable correlation between oxidizing ability. It established that highly (e.g. ⋅OCF 3 ) capable engaging single‐electron transfer (SET) processes rather than addition, which good agreement with experimental literature data. scale, based on barrier addition these benzene elaborated using high accuracy DLPNO‐(U)CCSD(T) method.

Language: Английский

Citations

21
Fluoroalkoxylating Reagents in Organic Synthesis: Recent Advances DOI
Mingxi Chen, Quande Wang

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)

Published: April 22, 2024

Abstract The fluoroalkoxy groups (OR f ) are widely used motifs in pharmaceutical and agrochemical fields due to their unique physicochemical properties including higher lipophilicity increased metabolic stability. Thus, the high value of OR ‐containing derivatives has stimulated development fluoroalkoxylation reactions. In this review, we highlight recent progress various trifluoroalkoxylating reagents applications organic synthesis past five years.

Language: Английский

Citations

4
2-Trifluoromethoxyacetic Acid – Synthesis and Characterization DOI Creative Commons

Thorsten Meier,

Sabine Lorenzen,

Tanja Knuplez

et al.

Journal of Fluorine Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 110396 - 110396

Published: Jan. 1, 2025

Language: Английский

Citations

0
Radical trifluoromethoxylation of fluorinated alkenes for accessing difluoro(trifluoromethoxy)methyl groups DOI Creative Commons

Koki Kawai,

Mai Usui,

Sota Ikawa

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

In this study, we explore the potential of difluoro(trifluoromethoxy)methyl group, CF 2 –O–CF 3 , an underexplored but promising structural analog trifluoromethoxy group (OCF ).

Language: Английский

Citations

0
Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications DOI
Shuai Liu, Jun Zhou, Lu Yu

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Language: Английский

Citations

0
Halo-perfluoroalkoxylation of gem-difluoroalkenes with short-lived alkali metal perfluoroalkoxides in triglyme DOI Creative Commons

Koki Kawai,

Yoshimitsu Kato,

Taichi Araki

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(25), P. 9574 - 9581

Published: Jan. 1, 2024

The synthesis of long-chain perfluoroalkyl ethers remains a challenge. stabilization longer-chain perfluoroalkoxides with triglyme-encapsulated potassium ions enabled the bis(α,α-difluoro)ethers gem -difluoroalkenes.

Language: Английский

Citations

3
N-Halosuccinimide enables cascade oxidative trifluorination and halogenative cyclization of tryptamine-derived isocyanides DOI Creative Commons

Jun‐Yunzi Wu,

Long-Ling Huang,

Junliang Fu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Oct. 16, 2024

Both the pyrroloindoline core and N-CF

Language: Английский

Citations

3
Catalyst‐Free Trifluoromethoxylation of Silyl Enol Ethers and Allyl Silanes with Bis(trifluoromethyl)peroxide DOI Creative Commons
Lilian M. Maas, Carlo Fasting, Patrick Voßnacker

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(7)

Published: Dec. 22, 2023

Abstract Radical trifluoromethoxylation is an attractive approach to prepare compounds featuring the important OCF 3 group, however most existing methods have focused on aromatic substrates. Here, we report novel methodologies with alkenyl substrates employing bis(trifluoromethyl)peroxide (BTMP) as a practical and comparatively atom economical trifluoromethoxylating reagent. With silyl enol ether substrates, switching reaction solvent allows for synthesis of either α‐(trifluoromethoxy)ketone products or unprecedented alkenyl‐OCF species. Furthermore, allyl silanes been employed first time, affording allyl(trifluoromethyl)ether in good yields. In each case, operate at room temperature without large excesses alkene substrate while, contrast previous radical reactions, no catalyst, light other activators are required.

Language: Английский

Citations

6
Review and Theoretical Analysis of Fluorinated Radicals in Direct CAr−H Functionalization of (Hetero)arenes DOI Creative Commons
Anthony J. Fernandes, Rahul Giri, K. N. Houk

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(16)

Published: Jan. 29, 2024

Abstract We highlight key contributions in the field of direct radical C Ar − H (hetero)aromatic functionalization involving fluorinated radicals. A compilation Functional Group Transfer Reagents and their diverse activation mechanisms leading to release radicals are discussed. The substrate scope for each is analyzed classified into three categories according electronic properties substrates. Density functional theory computational analysis provides insights chemical reactivity several through electrophilicity nucleophilicity parameters. Theoretical reduction potentials also highlights remarkable correlation between oxidizing ability. It established that highly (e.g. ⋅OCF 3 ) capable engaging single‐electron transfer (SET) processes rather than addition, which good agreement with experimental literature data. scale, based on barrier addition these benzene elaborated using high accuracy DLPNO‐(U)CCSD(T) method.

Language: Английский

Citations

1
4-Trifluoromethoxy proline: synthesis of stereoisomers and lipophilicity study DOI
Ivan G. Logvinenko,

Iryna V. Sadkova,

Nataliya A. Tolmachova

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(39), P. 7982 - 7988

Published: Jan. 1, 2024

All four stereoisomers of 4-CF

Language: Английский

Citations

1