Ligand-Enabled γ-C(sp3 )-H Activation of Ketones

Journal of the American Chemical Society
Ru-Yi ZhuJin-Quan Yu

Abstract

We report the first example of Pd(II)-catalyzed γ-C(sp3)-H activation of ketones directed by a practical 2,2-dimethyl aminooxyacetic acid auxiliary. 2-Pyridone ligands are identified to enable C(sp3)-H activation for the first time. A rare six-membered palladacycle intermediate is isolated and characterized to elucidate the reaction mechanism. Both (hetero)arylation and vinylation of γ-C(sp3)-H bonds are demonstrated. Sequential β- and γ-C(sp3)-H (hetero)arylation of muscone showcases the utility of this method for late-stage diversification. A convenient Mn(II)-catalyzed auxiliary removal is also developed to further underscore the practicality of this transformation.

Citations

Aug 30, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Houguang Jeremy ChenPak-Hing Leung
Nov 28, 2018·Chemistry : a European Journal·Luo-Yan LiuJin-Quan Yu
Nov 30, 2019·Angewandte Chemie·Bijin LiHaibo Ge
Feb 13, 2020·Angewandte Chemie·Guoqin XiaJin-Quan Yu
Apr 7, 2020·Angewandte Chemie·Kiron Kumar GhoshManuel van Gemmeren
Oct 2, 2020·Organic & Biomolecular Chemistry·Shi-Biao TangYa-Fei Ji
Feb 19, 2019·Chemical Science·Zuxiao ZhangDavid A Nagib
Apr 17, 2019·Nature Chemistry·Guoqin XiaJin-Quan Yu
Mar 1, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jagadeesh Kalepu, Lukasz T Pilarski
May 10, 2020·Angewandte Chemie·Han Seul ParkJin-Quan Yu
Jan 26, 2021·Chemical Communications : Chem Comm·Gaurav Saini, Manmohan Kapur
Jan 15, 2021·The Journal of Organic Chemistry·Peng-Peng NiuYu-Peng He
Dec 24, 2020·Chemical Communications : Chem Comm·Qiu-Zi WuDan-Qian Xu
May 6, 2021·The Journal of Organic Chemistry·Yangyang WangYafei Ji
May 22, 2021·Nature Communications·Yong ShangQianghui Zhou
Jun 8, 2021·Chemical Science·Jayabrata DasDebabrata Maiti
Jun 8, 2021·Chemical Science·Zhoulong FanJin-Quan Yu
Jun 25, 2021·Chemical Science·Trisha BhattacharyaDebabrata Maiti
Jun 23, 2021·Chemistry : a European Journal·Gao HuangChangduo Pan
Jun 26, 2018·Journal of the American Chemical Society·Baihua YeF Dean Toste
Aug 7, 2019·The Journal of Organic Chemistry·Diego Alemán-Ponce de LeónLuis A Polindara-García
Jul 20, 2019·Organic Letters·Aniket GuptaSukalyan Bhadra
Jun 22, 2019·ACS Catalysis·Hojoon ParkJin-Quan Yu
Oct 24, 2018·Journal of the American Chemical Society·Laura K G AckermanAbigail G Doyle
Dec 1, 2018·Journal of the American Chemical Society·Yan-Qiao ChenJin-Quan Yu

❮ 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.