ortho -Selective C-H addition of N ,N -dimethyl anilines to alkenes by a yttrium catalyst

Chemical Science
Guoyong SongZhaomin Hou

Abstract

The efficient and selective ortho-alkylation of N,N-dimethyl anilines via C-H addition to alkenes was achieved for the first time using a cationic half-sandwich yttrium catalyst. This protocol constitutes a straightforward and atom-economical route for the synthesis of a new family of tertiary aniline derivatives with branched alkyl substituents, which are otherwise difficult to obtain. DFT calculation studies suggest that the interaction between the yttrium atom and the NMe2 group plays an important role and the intramolecular C-H activation through a σ-bond metathesis pathway is the rate-determining step, which is consistent with the experimental KIE observations.

References

Jul 4, 2002·Journal of the American Chemical Society·Nick A Paras, David W C MacMillan
Jun 15, 2006·Chemical Reviews·Peter M ZeimentzJun Okuda
Jul 3, 2007·Organic Letters·Norito TakenakaSreehari Kumar Seerla
Sep 14, 2010·Chemical Reviews·Anders HagfeldtHenrik Pettersson
Dec 3, 2010·Nature Chemistry·Masayoshi Nishiura, Zhaomin Hou
Mar 25, 2011·Journal of the American Chemical Society·Laurean IliesEiichi Nakamura
Oct 18, 2011·Journal of the American Chemical Society·Bing-Tao Guan, Zhaomin Hou
Mar 21, 2013·Angewandte Chemie·Bing-Tao GuanZhaomin Hou
Aug 19, 2014·Journal of the American Chemical Society·Guoyong SongZhaomin Hou
Sep 16, 2014·Journal of the American Chemical Society·Xingbang HuGuy Bertrand
Apr 23, 2015·Chemistry : a European Journal·Guoyong SongZhaomin Hou
Jul 28, 2015·Accounts of Chemical Research·Masayoshi NishiuraZhaomin Hou

❮ Previous
Next ❯

Citations

Aug 15, 2018·Angewandte Chemie·Gwilherm Evano, Cédric Theunissen
Aug 10, 2020·Chemistry, an Asian Journal·Gaowen ZhaiXingbang Hu
Mar 25, 2020·Chemical Science·Supriya Rej, Naoto Chatani
Aug 5, 2017·Science Advances·Chunxiang WangZhaomin Hou
May 16, 2019·Chemical Communications : Chem Comm·Yanan ZhaoYi Luo
Feb 13, 2020·Chemistry, an Asian Journal·Wenxuan XuZhaomin Hou
Feb 3, 2021·Journal of the American Chemical Society·Shao-Jie LouZhaomin Hou
Mar 17, 2021·Chemical Communications : Chem Comm·Jianhong SuXin Xu
May 6, 2016·Journal of the American Chemical Society·Xiaochao ShiZhaomin Hou
Dec 21, 2017·Journal of the American Chemical Society·Yong LuoZhaomin Hou
Sep 29, 2020·Journal of the American Chemical Society·Shao-Jie LouZhaomin Hou
May 10, 2020·The Journal of Organic Chemistry·Tobias Taeufer, Jola Pospech
Jan 27, 2017·Chemical Reviews·Zhe DongGuangbin Dong
Dec 3, 2021·The Journal of Organic Chemistry·Gongming PengFrançois Jérôme

❮ 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.

Related Papers

Journal of the American Chemical Society
Bing-Tao Guan, Zhaomin Hou
Angewandte Chemie
Hideaki Wakamatsu, Siegfried Blechert
© 2022 Meta ULC. All rights reserved