Friedel-Crafts-Type Intermolecular C-H Silylation of Electron-Rich Arenes Initiated by Base-Metal Salts

Angewandte Chemie
Qin YinMartin Oestreich

Abstract

An electrophilic aromatic substitution (SE Ar) with a catalytically generated silicon electrophile is reported. Essentially any commercially available base-metal salt acts as an initiator/catalyst when activated with NaBAr(F)4. The thus-generated Lewis acid then promotes the SE Ar of electron-rich arenes with hydrosilanes but not halosilanes. This new C-H silylation was optimized for FeCl2/NaBAr(F)4, affording good yields at catalyst loadings as low as 0.5 mol %. The procedure is exceedingly straightforward and comes close to typical Friedel-Crafts methods, where no added base is needed to absorb the released protons.

References

Nov 22, 2000·Chemical & Pharmaceutical Bulletin·M YanagisawaT Mukaiyama
Oct 8, 2009·Journal of the American Chemical Society·Shunsuke FurukawaTakayuki Kawashima
Sep 11, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Shunsuke FurukawaTakayuki Kawashima
Apr 26, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Thomas J HerringtonAndrew E Ashley
Jun 28, 2012·Chemistry : a European Journal·Teruhisa TsuchimotoMasaru Sekine
Aug 10, 2012·Chemical Communications : Chem Comm·Shintaro ItagakiNoritaka Mizuno
Oct 18, 2012·Chemical Communications : Chem Comm·Simone G WeberBernd F Straub
Jan 22, 2014·Chemical Communications : Chem Comm·Lutz GrebJan Paradies
Mar 29, 2014·Organic Letters·Latisha R Jefferies, Silas P Cook
Aug 2, 2014·Journal of the American Chemical Society·Chen Cheng, John F Hartwig
Dec 17, 2014·Journal of the American Chemical Society·Chen Cheng, John F Hartwig
Feb 26, 2015·Chemical Reviews·Chen Cheng, John F Hartwig
Jul 17, 2015·Angewandte Chemie·Lukas Omann, Martin Oestreich
Jul 1, 2015·Chemical Science·Timo StahlMartin Oestreich

❮ Previous
Next ❯

Citations

Mar 10, 2016·Journal of the American Chemical Society·Yuanhong MaZhaomin Hou
Jun 16, 2016·Journal of the American Chemical Society·Qing-An ChenMartin Oestreich
Apr 20, 2017·Journal of the American Chemical Society·Elizabeth J RaymentEdward A Anderson
May 10, 2017·Journal of the American Chemical Society·Yuxi HanYuetao Zhang
Apr 7, 2016·Chemical Communications : Chem Comm·K DevarajL T Pilarski
Oct 26, 2016·Chemistry : a European Journal·Valerio FasanoMichael J Ingleson
Sep 20, 2016·Angewandte Chemie·Mark C LipkeT Don Tilley
Jul 20, 2018·Chemistry : a European Journal·Yasunori Minami, Tamejiro Hiyama
Mar 27, 2019·Chemical Communications : Chem Comm·Yan-Chen WuJin-Heng Li
Aug 14, 2019·Chemical Communications : Chem Comm·Xiu WangYasushi Nishihara
May 26, 2017·Chemical Society Reviews·Lucy PingSang-Gi Lee
Apr 11, 2020·Beilstein Journal of Organic Chemistry·Yafang DongYoichiro Kuninobu
Oct 10, 2020·Chemical Communications : Chem Comm·Mengxing LiRulong Yan
Dec 17, 2020·Chemical Society Reviews·Yuanhong MaZhaomin Hou
Apr 17, 2021·Chemical Reviews·Hendrik F T KlareMartin Oestreich
Jun 25, 2021·Chemical Communications : Chem Comm·Yafang DongYoichiro Kuninobu
Jul 2, 2021·Chemical Science·Matthew E GrundyMichael J Ingleson
Sep 30, 2017·Organic Letters·Zhengbao XuZhong-Quan Liu
Aug 14, 2021·Organic Letters·Wataru IshigaMamoru Tobisu
Nov 5, 2016·Organic Letters·Huaquan FangZheng Huang
Oct 3, 2018·Journal of the American Chemical Society·Jianbo ZhangSukbok Chang
Aug 25, 2017·Journal of the American Chemical Society·Yuanhong MaZhaomin Hou
Aug 19, 2017·Journal of the American Chemical Society·Bo Su, John F Hartwig

❮ 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.