Aerobic Asymmetric Dehydrogenative Cross-Coupling between Two C(sp3)-H Groups Catalyzed by a Chiral-at-Metal Rhodium Complex

Angewandte Chemie
Yuqi TanEric Meggers

Abstract

A sustainable C-C bond formation is merged with the catalytic asymmetric generation of one or two stereocenters. The introduced catalytic asymmetric cross-coupling of two C(sp3)-H groups with molecular oxygen as the oxidant profits from the oxidative robustness of a chiral-at-metal rhodium(III) catalyst and exploits an autoxidation mechanism or visible-light photosensitized oxidation. In the latter case, the catalyst serves a dual function, namely as a chiral Lewis acid for catalyzing enantioselective enolate chemistry and at the same time as a visible-light-driven photoredox catalyst.

References

Aug 2, 2008·Angewandte Chemie·Liang Zhao, Chao-Jun Li
Jan 15, 2010·Journal of the American Chemical Society·Allison G CondieCorey R J Stephenson
Jun 10, 2010·Chemical Society Reviews·Jagan M R Narayanam, Corey R J Stephenson
Jun 15, 2010·Angewandte Chemie·Aron PintérMartin Klussmann
Jun 24, 2010·Nature Chemistry·Tehshik P YoonJuana Du
Nov 2, 2011·Chemical Communications : Chem Comm·Magnus RuepingRené M Koenigs
Jan 31, 2012·The Journal of Organic Chemistry·Joseph W Tucker, Corey R J Stephenson
Feb 24, 2012·Chemical Society Reviews·Zhuangzhi ShiNing Jiao
Jun 20, 2012·Angewandte Chemie·Jun Xuan, Wen-Jing Xiao
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
May 30, 2013·Organic & Biomolecular Chemistry·Naeem Gulzar, Martin Klussmann
Jun 19, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Louise F GildeaJ A Gareth Williams
Apr 24, 2014·Journal of the American Chemical Society·Haohua HuoEric Meggers
Jul 9, 2014·Journal of the American Chemical Society·Joel W Beatty, Corey R J Stephenson
Oct 8, 2014·Angewandte Chemie·Congde HuoJing Tang
Oct 29, 2014·Chemical Communications : Chem Comm·Xiao-Hong WeiShang-Dong Yang
Jan 13, 2015·Chemical Communications : Chem Comm·Eric Meggers
Mar 3, 2015·Angewandte Chemie·Richard BrimioulleThorsten Bach
Apr 3, 2015·Chemistry : a European Journal·Chuanyong WangEric Meggers
May 8, 2015·Accounts of Chemical Research·Joel W Beatty, Corey R J Stephenson
Feb 1, 2015·Chemical Science·Chuanyong WangEric Meggers

❮ Previous
Next ❯

Citations

Apr 14, 2016·Chemical Reviews·Davide RavelliMaurizio Fagnoni
Aug 2, 2016·The Journal of Organic Chemistry·Megan H ShawDavid W C MacMillan
Dec 14, 2016·The Journal of Organic Chemistry·Jian-Qiang ChenPeng-Fei Xu
Dec 22, 2016·Journal of the American Chemical Society·Wei DingWen-Jing Xiao
Jan 28, 2017·Accounts of Chemical Research·Lilu Zhang, Eric Meggers
Mar 16, 2017·Journal of the American Chemical Society·Yu ZhengEric Meggers
May 27, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·María CarmonaDaniel Carmona
Feb 26, 2016·Chemical Communications : Chem Comm·Cheng TianEric Meggers
May 5, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Jiajia MaEric Meggers
May 28, 2016·Chemical Communications : Chem Comm·Liangliang SongEric Meggers
Jul 28, 2016·Chemical Communications : Chem Comm·Jiajia MaEric Meggers
Aug 8, 2017·Chemistry, an Asian Journal·Lilu Zhang, Eric Meggers
Nov 14, 2018·Chemical Communications : Chem Comm·Qiong YangShaolin Zhou
May 28, 2020·Organic & Biomolecular Chemistry·Bor-Cherng Hong
Mar 30, 2021·Journal of the American Chemical Society·Rupert S J ProctorRobert J Phipps
Mar 7, 2019·Accounts of Chemical Research·Xiaoqiang Huang, Eric Meggers
Jun 23, 2020·The Journal of Organic Chemistry·Xiao-De AnJian Xiao

❮ 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.