Nickel-catalyzed borylation of arenes and indoles via C-H bond cleavage

Chemical Communications : Chem Comm
Takayuki FurukawaNaoto Chatani

Abstract

The first nickel-catalyzed method for the borylation of carbon-hydrogen bonds in arenes and indoles is described. The use of an N-heterocyclic carbene ligand is essential for an efficient reaction, with an N-cyclohexyl-substituted derivative being optimal. This method is readily applied to the gram scale synthesis of 2-borylindole.

References

Jul 1, 2008·Accounts of Chemical Research·Benjamin D Sherry, Alois Fürstner
Nov 13, 2008·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Jun 16, 2009·Journal of the American Chemical Society·Naohiko YoshikaiEiichi Nakamura
Dec 24, 2009·Chemical Reviews·Ibraheem A I MkhalidJohn F Hartwig
Apr 29, 2010·Chemical Communications : Chem Comm·Guobing YanJianbo Wang
Jun 5, 2010·The Journal of Organic Chemistry·Eiichi Nakamura, Naohiko Yoshikai
Aug 10, 2010·Journal of the American Chemical Society·Meghan E DosterSamuel A Johnson
Oct 13, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Kyalo Stephen KanyivaSensuke Ogoshi
Nov 6, 2010·Chemical Reviews·Chang-Liang SunZhang-Jie Shi
Oct 26, 2011·Journal of the American Chemical Society·Mamoru TobisuNaoto Chatani
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
May 5, 2012·Accounts of Chemical Research·Sharon R Neufeldt, Melanie S Sanford
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Sep 6, 2012·Journal of the American Chemical Society·Maria N Eliseeva, Lawrence T Scott
Nov 21, 2012·Journal of the American Chemical Society·Alexey G SergeevJohn F Hartwig
Oct 1, 2013·Journal of the American Chemical Society·Thomas J Mazzacano, Neal P Mankad
Feb 14, 2014·Chemistry : a European Journal·Alex D SunJennifer A Love
Mar 1, 2014·Accounts of Chemical Research·Ke Gao, Naohiko Yoshikai
Mar 5, 2014·Journal of the American Chemical Society·Jennifer V ObligacionPaul J Chirik
Apr 2, 2014·Journal of the American Chemical Society·Mamoru TobisuNaoto Chatani
Aug 27, 2014·Chemical Society Reviews·Josep CornellaRuben Martin
Aug 30, 2014·Journal of the American Chemical Society·Joseph S BairJohn F Hartwig
Jan 15, 2015·Organic Letters·Mamoru TobisuNaoto Chatani

❮ Previous
Next ❯

Citations

Dec 30, 2015·Journal of the American Chemical Society·W Neil PalmerPaul J Chirik
Dec 3, 2015·The Journal of Organic Chemistry·Jiefeng HuZhuangzhi Shi
Dec 23, 2015·Chemistry : a European Journal·Luis C Misal CastroNaoto Chatani
May 16, 2015·Journal of the American Chemical Society·Cayetana ZarateRuben Martin
Sep 16, 2015·Journal of the American Chemical Society·Takayuki FurukawaNaoto Chatani
Dec 4, 2015·Organic Letters·Calum W MuirAllan J B Watson
Oct 6, 2015·Chemical Communications : Chem Comm·Jun TakayaNobuharu Iwasawa
Mar 24, 2016·Chemical Communications : Chem Comm·Marc-André LégaréFrédéric-Georges Fontaine
Mar 24, 2016·Journal of the American Chemical Society·Konstantin ChernichenkoTimo Repo
Jun 10, 2015·Journal of the American Chemical Society·Alex J NettJohn Montgomery
May 27, 2015·Organic Letters·Margaret L ScheuermannPaul J Chirik
Aug 2, 2016·Journal of the American Chemical Society·Jennifer V ObligacionPaul J Chirik
Aug 31, 2016·Topics in Current Chemistry·Junichiro YamaguchiKenichiro Itami
Sep 8, 2016·The Journal of Organic Chemistry·Akimichi OhtsukiNaoto Chatani
Jan 31, 2017·Chemistry : a European Journal·Étienne RochetteFrédéric-Georges Fontaine
Apr 28, 2017·Chemistry : a European Journal·Yun-Lin LiuGerhard Erker
Jun 15, 2017·Journal of the American Chemical Society·Matthew R Elsby, Samuel A Johnson
Jul 6, 2018·Chemical Communications : Chem Comm·Jompol ThongpaenOlivier Baslé
Sep 12, 2018·Angewandte Chemie·Qi ZhongHua Zhang
Feb 15, 2019·Chemistry : a European Journal·Yadong PangHajime Ito
Mar 15, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Nicolas Bouchard, Frédéric-Georges Fontaine
Aug 2, 2019·Angewandte Chemie·Jompol ThongpaenOlivier Baslé
Jun 25, 2016·Beilstein Journal of Organic Chemistry·Mamoru TobisuNaoto Chatani
Aug 1, 2015·Science·Marc-André LégaréFrédéric-Georges Fontaine
Dec 15, 2015·Beilstein Journal of Organic Chemistry·Johnathon YauDavid J Nelson
May 10, 2016·Chemical Communications : Chem Comm·Kimihiro KomeyamaKen Takaki
Oct 2, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marek ČubiňákTomáš Tobrman
Feb 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luke BrittonStephen P Thomas
Aug 2, 2017·Chemical Communications : Chem Comm·Zhixiong RuanLutz Ackermann
Mar 19, 2021·Organic Letters·Youliang ZouHua Zhang
Jun 2, 2021·Organic Letters·Wesley L PeinJohn Montgomery
Jul 22, 2021·Chemical Communications : Chem Comm·Antony P Y ChanAlexey G Sergeev
Oct 9, 2019·The Journal of Organic Chemistry·Toshiyuki KameiToyoshi Shimada
Aug 12, 2021·Chemical Science·Sehye MinYunho Lee
Aug 28, 2018·ACS Catalysis·Milton R SmithBuddhadeb Chattopadhyay
Apr 18, 2017·Journal of the American Chemical Society·Santanu Panda, Joseph M Ready

❮ 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.