Rh(III)-catalyzed intermolecular C-H amination of 1-aryl-1H-pyrazol-5(4H)-ones with alkylamines

Organic Letters
Kui WuAo Zhang

Abstract

An intermolecular C-H amination of 1-aryl-1H-pyrazol-5(4H)-ones was achieved under mild reaction conditions, using a low catalyst loading and with a broad scope of aminating reagents. This protocol not only provides the first example of rhodium(III)-catalyzed intermolecular aromatic C-H amination directed by an intrinsic functionality of the substrate/product but also features aminating an existing drug with either primary or secondary N-benzoate alkylamines as the coupling partners.

References

May 14, 2017·Angewandte Chemie·Huai-Wei WangJin-Quan Yu
Jul 2, 2014·Organic Letters·C Bryan HuehlsJiong Yang
Sep 26, 2015·Chemical Communications : Chem Comm·Bingxian LiuBaiquan Wang
Jul 29, 2017·Journal of the American Chemical Society·Charles E HendrickQiu Wang
Feb 13, 2015·Organic & Biomolecular Chemistry·Gang LiHankui Wu
Jan 20, 2015·Angewandte Chemie·Dajian ZhuJin-Quan Yu
Jun 27, 2020·Cancer Cell International·Xiongdong ZhongNi Gu

Citations

Apr 1, 1988·Stroke; a Journal of Cerebral Circulation·K AbeK Kogure
Jun 5, 2002·Neuroscience·M-Z YaoX-Y Liu
May 6, 2004·Journal of the American Chemical Society·Ashley M Berman, Jeffrey S Johnson
May 12, 2005·Angewandte Chemie·Huw M L Davies, Matthew S Long
Oct 20, 2005·Journal of the American Chemical Society·W C Peter TsangStephen L Buchwald
Nov 2, 2007·Chemical Reviews·Egle M BeccalliSilvia Sottocornola
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
Jul 30, 2008·Angewandte Chemie·David S Surry, Stephen L Buchwald
Oct 7, 2008·Journal of the American Chemical Society·Masayuki Wasa, Jin-Quan Yu
Nov 13, 2008·Journal of the American Chemical Society·James A Jordan-HoreMatthew J Gaunt
Aug 13, 2009·Angewandte Chemie·Julia J NeumannFrank Glorius
Aug 15, 2009·Angewandte Chemie·Florian Monnier, Marc Taillefer
Jan 30, 2010·Chemical Society Reviews·Ling-Min XuZhang-Jie Shi
Mar 2, 2010·Journal of the American Chemical Society·Yichen Tan, John F Hartwig
Aug 26, 2010·Journal of the American Chemical Society·Ka-Ho NgWing-Yiu Yu
Jun 15, 2011·Chemical Society Reviews·Joanna Wencel-DelordFrank Glorius
Dec 31, 2011·Journal of the American Chemical Society·Enrico T Nadres, Olafs Daugulis
May 5, 2012·Accounts of Chemical Research·Sharon R Neufeldt, Melanie S Sanford
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 22, 2012·Angewandte Chemie·Nadine KuhlFrank Glorius
Apr 26, 2013·Angewandte Chemie·Ly Dieu TranOlafs Daugulis

Related Concepts

Amination
Amines
Organometallic Compounds
Benzoates
Pyrazole
Aromatics
Catalysis
Pyrazolin-5-Ones
Benzoate
Rhodium

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.

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.

Synapse Loss as Therapeutic Target in MS

As we age, the number of synapses present in the human brain starts to decline, but in neurodegenerative diseases this occurs at an accelerated rate. In MS, it has been shown that there is a reduction in synaptic density, which presents a potential target for treatment. Here is the latest research on synapse loss as a therapeutic target in MS.

Artificial Intelligence in Cardiac Imaging

Artificial intelligence (ai) techniques are increasingly applied to cardiovascular (cv) medicine in cardiac imaging analysis. 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.

Social Learning

Social learning involves learning new behaviors through observation, imitation and modeling. Follow this feed to stay up to date on the latest research.

Cell Atlas of the Human Eye

Constructing a cell atlas of the human eye will require transcriptomic and histologic analysis over the lifespan. This understanding will aid in the study of development and disease. Find the latest research pertaining to the Cell Atlas of the Human Eye here.

Single Cell Chromatin Profiling

Techniques like ATAC-seq and CUT&Tag have the potential to allow single cell profiling of chromatin accessibility, histones, and TFs. This will provide novel insight into cellular heterogeneity and cell states. Discover the latest research on single cell chromatin profiling here.

Genetic Screens in iPSC-derived Brain Cells

Genetic screening is a critical tool that can be employed to define and understand gene function and interaction. This feed focuses on genetic screens conducted using induced pluripotent stem cell (iPSC)-derived brain cells.