Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes.

Chemical Science
Chao ChenBing Zhou

Abstract

Transition-metal-catalyzed directed C-H functionalization has emerged as a powerful and straightforward tool to construct C-C bonds and C-N bonds. Among these processes, the intramolecular annulative alkene hydroarylation reaction has received much attention because this intramolecular annulation can produce more complex and high value-added structural motifs found in numerous natural products and bioactive molecules. Despite remarkable progress, these annulative protocols developed to date remain limited to hydroarylation and functionalization of one side of alkenes, thus largely limiting the structural diversity and complexity. Herein, we developed a rhodium(iii)-catalyzed tandem annulative arylation/amidation reaction of aromatic tethered alkenes to deliver a variety of 2,3-dihydro-3-benzofuranmethanamine derivatives bearing an all-carbon quaternary stereo center by employing 3-substituted 1,4,2-dioxazol-5-ones as an amidating reagent to capture the transient C(sp3)-Rh intermediate. Notably, by simply changing the directing group, a second, unsymmetrical ortho C-H amidation/annulation can be achieved to provide tricyclic dihydrofuro[3,2-f]quinazolinones in good yields.

References

Sep 27, 2001·Journal of the American Chemical Society·R K ThaljiJ A Ellman
May 20, 2006·Nature Chemical Biology·Ryan Hili, Andrei K Yudin
Oct 9, 2007·Journal of the American Chemical Society·Wei Zeng, Sherry R Chemler
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Jun 24, 2009·Journal of the American Chemical Society·Carolyn F RosewallForrest E Michael
Jan 7, 2010·Journal of the American Chemical Society·Guozhu ZhangLiming Zhang
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Aug 27, 2010·Chemistry : a European Journal·Tetsuya Satoh, Masahiro Miura
Dec 14, 2011·Accounts of Chemical Research·Denise A ColbyJonathan A Ellman
Dec 31, 2011·Journal of the American Chemical Society·Enrico T Nadres, Olafs Daugulis
Jan 20, 2012·Journal of the American Chemical Society·Timothy W Liwosz, Sherry R Chemler
Mar 2, 2012·Chemical Society Reviews·Guoyong SongXingwei Li
May 2, 2012·Accounts of Chemical Research·Jennifer L RoizenJ Du Bois
May 26, 2012·Journal of the American Chemical Society·Ji Young KimSukbok Chang
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
May 29, 2013·Journal of the American Chemical Society·Da-Gang YuFrank Glorius
Jun 4, 2013·Organic Letters·Christoph GrohmannFrank Glorius
Sep 4, 2013·Journal of the American Chemical Society·Gregory B BoursalianTobias Ritter
Jan 24, 2014·Journal of the American Chemical Society·Sae Hume ParkSukbok Chang
Jan 29, 2014·Chemical Communications : Chem Comm·Zhuangzhi ShiFrank Glorius
Mar 29, 2014·Chemistry : a European Journal·Juanjuan DuBing Zhou
Aug 21, 2014·Nature Communications·Mingyu YangZhang-Jie Shi
Jan 17, 2015·Chemical Reviews·Beverley M Dancy, Philip A Cole
Jan 20, 2015·Angewandte Chemie·Dajian ZhuJin-Quan Yu
Apr 7, 2015·Accounts of Chemical Research·Guoyong Song, Xingwei Li

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Methods Mentioned

BETA
amidation
column chromatography
X-ray

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.