Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides

Organic Letters
Saurabh MaityRajarshi Samanta

Abstract

A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.

References

Jun 16, 2005·Neuro-Signals·Chihiro TohdaKatsuko Komatsu
Aug 16, 2006·Accounts of Chemical Research·Rebecca M Wilson, Samuel J Danishefsky
May 11, 2007·Bioorganic & Medicinal Chemistry Letters·Anna R McCarthyAndrew D Abell
May 29, 2009·Organic Letters·Dachen Cheng, Timothy Gallagher
Oct 20, 2009·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Jan 21, 2010·Chemical Communications : Chem Comm·Chang-Liang SunZhang-Jie Shi
Jun 10, 2010·Natural Product Reports·Henning Jacob Jessen, Karl Gademann
Jun 15, 2011·Chemical Society Reviews·Joanna Wencel-DelordFrank Glorius
Jul 30, 2011·Organic Letters·Henning J JessenKarl Gademann
Aug 9, 2011·Organic Letters·Anna D Fotiadou, Alexandros L Zografos
Apr 21, 2012·Angewandte Chemie·Ryuichi TamuraTamejiro Hiyama
Nov 3, 2012·Organic Letters·Anna D Fotiadou, Alexandros L Zografos
Jun 6, 2013·Chemical Communications : Chem Comm·Shao-Jie LouZhen-Yuan Xu
Jun 12, 2013·The Journal of Organic Chemistry·Yi-Yun YuGunda I Georg
May 20, 2014·Chemical Communications : Chem Comm·Elissavet E AnagnostakiAlexandros L Zografos
Jul 22, 2014·Angewandte Chemie·Shao-Jie LouZhen-Yuan Xu
Jul 23, 2014·Chemistry, an Asian Journal·Feiqing DingXue-Wei Liu
Nov 26, 2014·The Journal of Organic Chemistry·Atanu ModakDebabrata Maiti
Feb 27, 2015·Accounts of Chemical Research·Karl Gademann
Apr 25, 2015·Angewandte Chemie·Peter SchröderHerbert Waldmann
Jul 28, 2015·Angewandte Chemie·Ian J S Fairlamb
Oct 23, 2015·Chemical Communications : Chem Comm·Uttam DuttaDebabrata Maiti
Dec 29, 2015·The Journal of Organic Chemistry·Yunyun LiXingwei Li
Jan 9, 2016·The Journal of Organic Chemistry·Debapratim DasRajarshi Samanta
Mar 13, 2017·Bioorganic & Medicinal Chemistry·Andrea ChiccaKarl Gademann
Apr 28, 2017·The Journal of Organic Chemistry·Wataru MiuraMasahiro Miura
May 26, 2017·Chemical Society Reviews·Lucy PingSang-Gi Lee
Jun 18, 2017·Organic & Biomolecular Chemistry·K Anil KumarParthasarathi Das
Sep 14, 2017·The Journal of Organic Chemistry·Aniruddha BiswasRajarshi Samanta
Sep 28, 2017·The Journal of Organic Chemistry·Shi-Yong ChenHonggen Wang
Oct 28, 2017·Chemical Communications : Chem Comm·Saurabh MaityRajarshi Samanta
Mar 16, 2018·Journal of the American Chemical Society·Johannes DieselNicolai Cramer
Jul 7, 2018·Beilstein Journal of Organic Chemistry·Erwann GrenetJérôme Waser

❮ Previous
Next ❯

Citations

Jan 3, 2019·Organic & Biomolecular Chemistry·Virendra Kumar Tiwari, Manmohan Kapur
Jun 21, 2019·Organic & Biomolecular Chemistry·Kunita Phakdeeyothin, Sirilata Yotphan
Feb 9, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Feiyue Hao, Nagatoshi Nishiwaki
Mar 18, 2020·Chemical Communications : Chem Comm·Animesh DasBiplab Maji
Oct 2, 2020·Organic & Biomolecular Chemistry·Ujjwal Karmakar, Rajarshi Samanta

❮ Previous
Next ❯

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.