Facile Access to Hetero-poly-functional Arenes and meta-Substituted Arenes via Two-Step Dimetalation and Mg/Halogen-Exchange Protocol.

Chemistry : a European Journal
Sonia BruñaCharles T O'Hara

Abstract

The Grignard reagent, iPrMgCl and its lithium chloride-enhanced 'turbo' derivative iPrMgCl⋅LiCl have been employed to investigate the single iodo/magnesium exchange reactions of the trisubstituted arenes, 2,5-diiodo-N,N-diisopropylbenzamide 1, 1,4-diiodo-2-methoxybenzene 2, and 1,4-diiodo-2-(trifluoromethyl)benzene 3. These three arenes themselves were initially prepared by a double ortho-, meta'-deprotonation of N,N-diisopropylbenzamide, anisole and (trifluoromethyl)benzene, respectively, using the sodium magnesiate reagent [Na4 Mg2 (TMP)6 (nBu)2 ] (where TMP is 2,2,6,6-tetramethylpiperidide), and subsequent electrophilic quenching with iodine/THF solution. Thus, by following a combined deprotonation and magnesium/halogen exchange strategy, the simple monosubstituted arenes can be converted to trisubstituted diiodoarenes, which can ultimately be transformed into the corresponding mono-magnesiated arenes, in THF at -40 °C, within seconds in good yields. The other functional group (OMe, NiPr2 or CF3 respectively) present on the di-iodoarenes helps direct the exchange reaction to the ortho position, whereas subsequent addition of different electrophiles permits the preparation of hetero-poly-functional-arenes, with three differen...Continue Reading

References

Mar 29, 2002·Chemistry : a European Journal·Ryan A BraggJennifer H Pink
May 9, 2002·Chemical Reviews·Jwanro HassanMarc Lemaire
Apr 1, 1959·Journal of Medicinal and Pharmaceutical Chemistry·H L YALE
Nov 25, 2003·The Journal of Organic Chemistry·Claus ChristophersenPer Vedsø
Jul 17, 2004·The Journal of Organic Chemistry·Thomas A JensenNiels Skjaerbaek
Mar 25, 2005·The Journal of Organic Chemistry·Ioannis SapountzisPaul Knochel
Jul 2, 2005·Angewandte Chemie·K C NicolaouDavid Sarlah
Feb 9, 2006·Chemical Communications : Chem Comm·Hongjun Ren, Paul Knochel
Sep 29, 2007·Science·Klaus MüllerFrançois Diederich
Jun 24, 2008·Journal of Medicinal Chemistry·William K Hagmann
Mar 21, 2009·Science·Robert J Phipps, Matthew J Gaunt
Mar 10, 2010·Proceedings of the National Academy of Sciences of the United States of America·Eva HeviaMatthew D McCall
Apr 5, 2011·Chemical Reviews·Olesya A Tomashenko, Vladimir V Grushin
Apr 21, 2011·Chemistry : a European Journal·Dongbing ZhaoChangwei Hu
Apr 28, 2011·Journal of the American Chemical Society·Bo ChenYun-Dong Wu
Oct 17, 2012·Chemistry : a European Journal·Christoph SämannPaul Knochel
Mar 29, 2013·Journal of the American Chemical Society·Nora Hofmann, Lutz Ackermann
Nov 6, 2013·Chemical Reviews·David TillyPhilippe C Gros
Dec 4, 2013·Journal of Medicinal Chemistry·Thomas G Gant
Dec 12, 2013·Journal of the American Chemical Society·Sunggi LeeKian L Tan
Feb 26, 2015·Chemical Communications : Chem Comm·Robert Li-Yuan BaoLei Shi
Jun 8, 2017·Nature Biotechnology·Charles Schmidt
May 15, 2018·Frontiers in Chemistry·Gwilherm EvanoDamien F Dewez
Sep 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sungsoo KimKyungwon Kwak
Sep 20, 2018·Chemistry : a European Journal·Dorothée S ZieglerPaul Knochel
Jan 15, 2019·Journal of Medicinal Chemistry·Tracey PiraliArmando A Genazzani
Mar 20, 2019·Chemical Reviews·Stuart D RobertsonRobert E Mulvey
Aug 27, 2019·Journal of the American Chemical Society·Luo-Yan LiuJin-Quan Yu
Nov 20, 2019·Chemistry : a European Journal·Moritz Balkenhohl, Paul Knochel
Apr 4, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Callum YeardleyCharles T O'Hara
Apr 26, 2020·Angewandte Chemie·Luo-Yan LiuJin-Quan Yu

❮ 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.