Transition-Metal-Free Activation of Amide Bond by Arynes

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Hideto Miyabe

Abstract

Highly reactive arynes activate the N⁻C and C=O bonds of amide groups under transition metal-free conditions. This review highlights the insertion of arynes into the N⁻C and C=O bonds of the amide group. The insertion of arynes into the N⁻C bond gives the unstable four-membered ring intermediates, which are easily converted into ortho-disubstituted arenes. On the other hand, the selective insertion of arynes into the C=O bond is observed when the sterically less-hindered formamides are employed to give a reactive transient intermediate. Therefore, the trapping reactions of transient intermediates with a variety of reactants lead to the formation of oxygen atom-containing heterocycles. As relative functional groups are activated, the reactions of arynes with sulfinamides, phosphoryl amides, cyanamides, sulfonamides, thioureas, and vinylogous amides are also summarized.

References

Feb 6, 2003·Angewandte Chemie·Hans Henning WenkWolfram Sander
Sep 22, 2005·Journal of the American Chemical Society·Zhijian Liu, Richard C Larock
May 25, 2011·Chemical Communications : Chem Comm·Hiroto YoshidaJoji Ohshita
Aug 24, 2011·Organic Letters·Kallolmay Biswas, Michael F Greaney
Mar 17, 2012·Angewandte Chemie·Christian M Gampe, Erick M Carreira
Mar 27, 2012·Chemical Reviews·Pamela M Tadross, Brian M Stoltz
Jul 19, 2013·Organic Letters·Eito YoshiokaHideto Miyabe
Jan 15, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Eito YoshiokaHideto Miyabe
Jan 18, 2014·The Journal of Organic Chemistry·Ran LiFeng Shi
Sep 18, 2014·Chemical Communications : Chem Comm·Adam E GoetzNeil K Garg
Dec 4, 2014·Accounts of Chemical Research·Wen-Ju BaiThomas R R Pettus
Jul 18, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hideto Miyabe
Jul 28, 2015·The Journal of Organic Chemistry·Eito YoshiokaHideto Miyabe
Jan 15, 2016·Angewandte Chemie·Catherine M HoldenMichael F Greaney
Jan 27, 2016·Chemical Society Reviews·Rajdip Karmakar, Daesung Lee
Mar 19, 2016·Journal of the American Chemical Society·Tejas K ShahNeil K Garg
Jun 9, 2016·The Journal of Organic Chemistry·Li-Rong WenMing Li
Aug 26, 2016·Accounts of Chemical Research·Sachin Suresh BhojgudeAkkattu T Biju
Oct 19, 2016·Chemical Society Reviews·José-Antonio García-López, Michael F Greaney
Feb 22, 2017·Chemical Society Reviews·Jiarong ShiYang Li
Apr 12, 2018·Organic & Biomolecular Chemistry·Kashmiri NeogPranjal Gogoi

❮ Previous
Next ❯

Citations

Mar 18, 2020·Chemistry : a European Journal·Helge LangeWolfram W Seidel
Jan 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fei ZhaoHong Liu
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
Jan 21, 2021·The Journal of Organic Chemistry·Abhilash SharmaPranjal Gogoi
Sep 29, 2020·The Journal of Organic Chemistry·Eito YoshiokaHideto Miyabe

❮ 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.

© 2022 Meta ULC. All rights reserved