C5-Regioselective C-H fluorination of 8-aminoquinoline amides and sulfonamides with Selectfluor under metal-free conditions

Organic & Biomolecular Chemistry
Yingchao ZhangJizhen Li

Abstract

A novel and efficient regioselective C-H fluorination of 8-aminoquinoline amides and sulfonamides at the C5 position was achieved. Using Selectfluor as a "F" reagent and HOAc as an additive, the reaction proceeds smoothly via a radical pathway. This method features metal-free conditions, a broad substrate scope and operational simplicity.

References

Aug 27, 2010·The Journal of Organic Chemistry·Dmitry V LiskinForrest E Michael
Dec 18, 2010·Journal of Natural Products·Robert S H Liu, Jin Liu
Mar 2, 2012·Chemical Society Reviews·Guoyong SongXingwei Li
Jun 29, 2012·Nature·Dasheng LeowJin-Quan Yu
Aug 7, 2012·Journal of the American Chemical Society·Timothy J Barker, Dale L Boger
Jun 6, 2013·Journal of the American Chemical Society·Erica L IngallsForrest E Michael
Jun 12, 2013·Journal of the American Chemical Society·Alison M SuessShannon S Stahl
Jun 14, 2013·Journal of the American Chemical Society·Thanh TruongOlafs Daugulis
Nov 19, 2013·Journal of the American Chemical Society·Li WanJin-Quan Yu
Mar 14, 2014·Nature·Ri-Yuan TangJin-Quan Yu
Jun 17, 2014·Chemical Communications : Chem Comm·Choon Wee KeeChoon-Hong Tan
Jun 20, 2014·Journal of the American Chemical Society·Cody Ross PittsThomas Lectka
Jul 18, 2015·Chemical Reviews·Shashank Mishra, Stéphane Daniele
Aug 4, 2015·Chemical Reviews·Alessandra VitaleBruno Ameduri
Aug 13, 2015·Journal of Medicinal Chemistry·J David BechererJohn C Ulrich
Nov 26, 2015·Bioorganic & Medicinal Chemistry Letters·Jizhen LiKuo-Hsiung Lee
Jan 13, 2016·Chemistry, an Asian Journal·Xiaogang LiuZhongfu An
Jan 21, 2016·Chemistry : a European Journal·Harekrishna SahooMahiuddin Baidya
Feb 19, 2016·Organic & Biomolecular Chemistry·Jun XuPengfei Zhang
Aug 11, 2016·Organic & Biomolecular Chemistry·Damian E YerienAl Postigo
Aug 11, 2016·Organic & Biomolecular Chemistry·Yoichiro KuninobuMotomu Kanai
Dec 23, 2016·The Journal of Organic Chemistry·Chenxi WangXiaoming Zhao
Jun 29, 2017·Organic Letters·Feifan WangWu Zhang

❮ Previous
Next ❯

Citations

May 11, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rebeka JójártErzsébet Mernyák
Jun 12, 2020·Topics in Current Chemistry·Zhihui XuRenhua Qiu
Dec 29, 2020·Chemical Communications : Chem Comm·Neshat Rozatian, David R W Hodgson
May 26, 2021·The Journal of Organic Chemistry·Zengxin QinJizhen Li
Aug 14, 2021·Beilstein Journal of Organic Chemistry·Teruo UmemotoGerald B Hammond
Aug 7, 2018·The Journal of Organic Chemistry·Qing YuYunyun Liu

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray
column chromatography
NMR

Software Mentioned

Selectfluor

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.