Transition Metal Free Cycloamination of Prenyl Carbamates and Ureas Promoted by Aryldiazonium Salts.

Angewandte Chemie
Roman AbramsJonathan Clayden

Abstract

Upon treatment with aryldiazonium salts, prenyl carbamates and ureas undergo redox-neutral azocycloamination. In general, N-aryl O-prenyl carbamates cyclize in a photocatalytic reaction with visible light and an organic dye. With electron-deficient diazonium salts, electronic matching with an electron-rich N-aryl substituent results in a reaction proceeding in the ground state, without either light or photocatalyst. Cyclic voltammetry suggests that this radical reaction is initiated by hydrogen-atom abstraction mediated by an aryl radical, followed by a radical addition cascade and proton-coupled hole propagation. The reaction proceeds at room temperature in short reaction times, and a range of functional groups is tolerated.

References

Apr 4, 1997·The Journal of Organic Chemistry·Hiroto HarayamaYoshinao Tamaru
Oct 24, 2001·The Journal of Organic Chemistry·Masao FujitaTakeo Taguchi
Feb 19, 2002·Chemical Reviews·Mogens Johannsen, Karl Anker Jørgensen
Apr 16, 2003·Accounts of Chemical Research·Stephen J Blanksby, G Barney Ellison
Mar 25, 2005·The Journal of Organic Chemistry·Stefan F Kirsch, Larry E Overman
May 26, 2005·Journal of the American Chemical Society·Erik J AlexanianErik J Sorensen
Jun 2, 2006·Organic Letters·Jonathan A FritzJohn P Wolfe
Mar 20, 2010·The Journal of Organic Chemistry·Brandon R RosenJohn P Wolfe
Jul 31, 2010·Angewandte Chemie·Fatima C SequeiraSherry R Chemler
Mar 20, 2013·Journal of the American Chemical Society·Zhaodong LiChaozhong Li
May 11, 2013·Journal of the American Chemical Society·Deshun HuangYian Shi
Aug 21, 2013·Chemical Communications : Chem Comm·Tao WuGuosheng Liu
Jan 15, 2014·Journal of the American Chemical Society·Haitao ZhuGuosheng Liu
May 16, 2014·Organic Letters·Deng-Fu LuHao Xu
Aug 22, 2014·Nature Chemistry·Armido Studer, Dennis P Curran
Aug 26, 2014·Chemistry : a European Journal·Fan XuHai-Chao Xu
Jul 15, 2015·Journal of the American Chemical Society·Gilbert J Choi, Robert R Knowles
Aug 22, 2015·Chemical Society Reviews·Nicholas A Butt, Wanbin Zhang
Oct 7, 2015·Journal of the American Chemical Society·David C MillerRobert R Knowles
Dec 5, 2015·Organic Letters·Stephanie KindtMarkus R Heinrich
Jun 9, 2016·Angewandte Chemie·Stephanie KindtMarkus R Heinrich
Sep 19, 2017·Journal of the American Chemical Society·Lena PitzerFrank Glorius
Jul 1, 2015·Chemical Science·Kun Shen, Qiu Wang

❮ Previous
Next ❯

Citations

Apr 19, 2019·Angewandte Chemie·Julio Romero-IbañezFernando Sartillo-Piscil
Nov 2, 2019·Nature Communications·Chen-Yan CaiHai-Chao Xu
Apr 23, 2021·Organic & Biomolecular Chemistry·Jiabin ShenPengfei Zhang
Dec 12, 2018·The Journal of Organic Chemistry·Yan-Na MaXuenian Chen
May 14, 2020·Organic Letters·Zhichao LuGerald B Hammond
May 3, 2019·Journal of the American Chemical Society·Daria KurandinaVladimir Gevorgyan
Sep 5, 2020·Organic Letters·Luana CardinaleAxel Jacobi von Wangelin
Feb 15, 2020·The Journal of Organic Chemistry·Ricardo A AngnesGerald B Hammond

❮ 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.