Phenyltrimethylammonium Salts as Methylation Reagents in the Nickel-Catalyzed Methylation of C-H Bonds

Angewandte Chemie
Takeshi UemuraNaoto Chatani

Abstract

Methylation of C(sp(2) )-H bonds was achieved through the Ni(II) -catalyzed reaction of benzamides with phenyltrimethylammonium bromide or iodide as the source of the methyl group. The reaction has a broad scope and shows high functional-group compatibility. The reaction is also applicable to the methylation of C(sp(3) )-H bonds in aliphatic amides.

References

Jun 6, 2003·Journal of the American Chemical Society·Simon B Blakey, David W C MacMillan
Mar 6, 2007·Journal of the American Chemical Society·Ramesh GiriJin-Quan Yu
Feb 14, 2008·Journal of the American Chemical Society·Yuhua ZhangChao-Jun Li
Feb 24, 2010·Journal of the American Chemical Society·Dmitry Shabashov, Olafs Daugulis
Apr 28, 2011·Angewandte Chemie·Lan-Gui Xie, Zhong-Xia Wang
Dec 14, 2011·Accounts of Chemical Research·Denise A ColbyJonathan A Ellman
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Mar 13, 2012·The Journal of Organic Chemistry·Xue-Qi Zhang, Zhong-Xia Wang
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Jan 29, 2013·Journal of the American Chemical Society·Shu-Yu ZhangGong Chen
Oct 24, 2013·Angewandte Chemie·Heike Schönherr, Tim Cernak
Jan 22, 2014·Organic & Biomolecular Chemistry·Xue-Qi Zhang, Zhong-Xia Wang
Mar 13, 2014·Journal of the American Chemical Society·Jinghan GuiPhil S Baran
Mar 14, 2014·Chemistry : a European Journal·Luis C Misal Castro, Naoto Chatani
Jul 2, 2014·Chemical Society Reviews·Fengzhi Zhang, David R Spring
Sep 11, 2014·Journal of the American Chemical Society·Ru-Yi ZhuJin-Quan Yu
May 8, 2015·Chemistry : a European Journal·Karolina GraczykLutz Ackermann
Jun 11, 2015·Journal of the American Chemical Society·Rui ShangEiichi Nakamura
Aug 1, 2015·Angewandte Chemie·Stefan A KünziPeter Chen
Aug 20, 2015·Angewandte Chemie·Christopher J TeskeyMichael F Greaney
Oct 6, 2015·Chemistry : a European Journal·Hua ZhangKenichiro Itami

❮ Previous
Next ❯

Citations

Oct 7, 2016·Chemical Communications : Chem Comm·Roberta CaporasoAndrey P Antonchick
Aug 18, 2017·Angewandte Chemie·Florian D'AccriscioNoel Nebra
Sep 5, 2018·Organic & Biomolecular Chemistry·Debashruti BandyopadhyayS Peruncheralathan
Sep 22, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ashish A MishraBhalchandra M Bhanage
Oct 1, 2016·Nature Communications·Dong-Yu WangMasanobu Uchiyama
Oct 18, 2018·Chemistry : a European Journal·Yantao Chen
Aug 15, 2018·Angewandte Chemie·Gwilherm Evano, Cédric Theunissen
Jun 18, 2019·Angewandte Chemie·Jelte S SteenJohannes E M N Klein
Jan 29, 2020·Organic & Biomolecular Chemistry·Zhong-Xia Wang, Bo Yang
Jan 30, 2020·Chemistry : a European Journal·Yuanhong MaJosep Cornella
Oct 21, 2016·Chemistry : a European Journal·Ze-Kun YangMasanobu Uchiyama
Apr 24, 2020·Angewandte Chemie·Ramesh C SamantaLutz Ackermann
Mar 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Noel Nebra
Aug 2, 2017·Chemical Communications : Chem Comm·Zhixiong RuanLutz Ackermann
Aug 24, 2017·Chemistry, an Asian Journal·Dong-Yu WangMasanobu Uchiyama
Apr 21, 2018·Chemical Science·Brandon E HainesDjamaladdin G Musaev
Aug 31, 2016·Topics in Current Chemistry·Junichiro YamaguchiKenichiro Itami
Sep 16, 2020·Angewandte Chemie·Prithwish GhoshIn Su Kim
Mar 11, 2021·Chemical Society Reviews·Daniya AynetdinovaDarren J Dixon
Jun 15, 2021·Chemical Science·Jack B WashingtonMarc Reid
Sep 7, 2018·Journal of the American Chemical Society·D Dawson BeattieJennifer A Love
Sep 13, 2019·Journal of the American Chemical Society·Qianwen GaoQianghui Zhou
Aug 19, 2021·The Journal of Organic Chemistry·Youjung ByunIn Su Kim
Jun 30, 2019·The Journal of Organic Chemistry·Weiwei LvGuolin Cheng
Dec 15, 2020·The Journal of Organic Chemistry·Rina SikariNanda D Paul

❮ 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.