Ring‐Opening Fluorination of Carbo/Heterocycles and Aromatics: Construction of Complex and Diverse Fluorine‐Containing Molecules DOI
Masaaki Komatsuda, Junichiro Yamaguchi

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(9)

Published: Jan. 5, 2023

Abstract Fluorine‐containing molecules have attracted much attention in medicinal, agrochemical, and materials sciences because they offer unique physical biological properties. Therefore, many efficient fluorination reactions been developed over the years. Recent advancements chemistry expanded range of substrates, regioselectivity/stereoselectivity control has also achieved. Ring‐opening is an method to construct complex fluorine‐containing with diversity, starting from simple cyclic compounds. This review aims summarize developments ring‐opening fluorination, particularly larger‐sized Fluorine introduction bond cleavage compounds such as carbocycles, heterocycles, aromatics provide access that are difficult be synthesized by conventional methods.

Language: Английский

Synthesis of 2-aminobenzofurans via base-mediated [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes DOI
Kaifeng Chen, Weijie Chen, Fangyuan Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(16), P. 4452 - 4458

Published: Jan. 1, 2021

Efficient metal-free [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes has been realized for the assembly 2-aminobenzofuran derivatives potent cytotoxicity against cancer cell lines and application potential DELs.

Language: Английский

Citations

22
Strategies for the Synthesis of Fluorinated Nucleosides, Nucleotides and Oligonucleotides DOI

Harshita Shet,

Rajesh Sahu,

Yogesh S. Sanghvi

et al.

The Chemical Record, Journal Year: 2022, Volume and Issue: 22(9)

Published: May 31, 2022

Abstract Fluorinated nucleosides and oligonucleotides are of specific interest as probes for studying nucleic acids interaction, structures, biological transformations, its biomedical applications. Among various modifications oligonucleotides, fluorination preformed nucleoside and/or nucleotides have recently gained attention owing to the unique properties fluorine atoms imparting medicinal with respect small size, electronegativity, lipophilicity, ability stereochemical control. This review deals synthetic protocols selective either at sugar or base moiety in a nucleosides, using fluorinating reagents.

Language: Английский

Citations

16
An N-Fluorinated Imide for Practical Catalytic Imidations DOI

Yuno Oe,

Ryuhei Yoshida,

Airi Tanaka

et al.

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(5), P. 2107 - 2113

Published: Jan. 27, 2022

Catalytic imidation using NFSI as the nitrogen source has become an emerging tool for oxidative carbon-nitrogen bond formation. However, less than ideal benzenesulfonimide moiety is incorporated into products, severely detracting its synthetic value. As a solution to this challenge, we report herein development of novel N-fluorinated imide, N-fluoro-N-(fluorosulfonyl)carbamate (NFC), by which attached imide acts modular handle one-step derivatization amines, sulfonamides, and sulfamides. Furthermore, study revealed superior reactivity NFC showcased in copper-catalyzed benzene derivatives imidocyanation aliphatic alkenes, overcoming limitation NFSI-mediated reactions.

Language: Английский

Citations

15
Oxidations of Alcohols, Aldehydes, and Diols Using NaBr and Selectfluor DOI
Harshit Joshi, Debobrata Paul, Shyam Sathyamoorthi

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 11240 - 11252

Published: July 25, 2023

We present protocols for the oxidation of alcohols and aldehydes oxidative cyclization diols which use a combination Selectfluor NaBr. For most substrates, optimal solvent system is 1:1 mixture CH3CN/H2O, but, in select cases, biphasic mixtures EtOAc/H2O or CH2Cl2/H2O are superior. This procedure operationally simple, uses inexpensive readily available reagents, tolerates variety functional groups. Mechanistic studies suggest that active oxidant hypobromous acid, generated by almost instantaneous Br– an aqueous milieu.

Language: Английский

Citations

9
Ring‐Opening Fluorination of Carbo/Heterocycles and Aromatics: Construction of Complex and Diverse Fluorine‐Containing Molecules DOI
Masaaki Komatsuda, Junichiro Yamaguchi

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(9)

Published: Jan. 5, 2023

Abstract Fluorine‐containing molecules have attracted much attention in medicinal, agrochemical, and materials sciences because they offer unique physical biological properties. Therefore, many efficient fluorination reactions been developed over the years. Recent advancements chemistry expanded range of substrates, regioselectivity/stereoselectivity control has also achieved. Ring‐opening is an method to construct complex fluorine‐containing with diversity, starting from simple cyclic compounds. This review aims summarize developments ring‐opening fluorination, particularly larger‐sized Fluorine introduction bond cleavage compounds such as carbocycles, heterocycles, aromatics provide access that are difficult be synthesized by conventional methods.

Language: Английский

Citations

8