Platinum-catalyzed domino reaction with benziodoxole reagents for accessing benzene-alkynylated indoles

Angewandte Chemie
Yifan Li, Jérôme Waser

Abstract

Indoles are omnipresent in natural products, bioactive molecules, and organic materials. Consequently, their synthesis or functionalization are important fields of research in organic chemistry. Most works focus on installation or modification of the pyrrole ring. To access benzene-ring-functionalized indoles with an unsubstituted pyrrole ring remains more challenging. Reported herein is a platinum-catalyzed cyclization/alkynylation domino process to selectively obtain C5- or C6-functionalized indoles starting from easily available pyrroles. The work combines, for the first time, a platinum catalyst with ethynylbenziodoxole hypervalent iodine reagents in a domino process for the synthesis of polyfunctionalized arene rings and gives access to important building blocks for the synthesis of bioactive compounds and organic materials.

References

Sep 20, 1996·The Journal of Organic Chemistry·Viktor V. ZhdankinAngela J. Simonsen
Feb 1, 1996·Chemical Reviews·Lutz F. Tietze
Jun 2, 2005·Journal of the American Chemical Society·Benjamin S LaneDalibor Sames
Apr 13, 2006·Journal of the American Chemical Society·Nicholas R DeprezMelanie S Sanford
Mar 23, 2007·Nature·David J Gorin, F Dean Toste
Apr 13, 2007·Angewandte Chemie·Alois Fürstner, Paul W Davies
May 16, 2007·Journal of the American Chemical Society·Tammene NaddoLing Zang
Jun 22, 2007·Chemical Reviews·A Stephen K Hashmi
Jun 12, 2008·Journal of the American Chemical Society·Robert J PhippsMatthew J Gaunt
Apr 11, 2009·Chemistry, an Asian Journal·José BarluengaFrancisco J Fañanás
Nov 7, 2009·Angewandte Chemie·Jonathan P BrandJérôme Waser
Jan 22, 2010·Journal of the American Chemical Society·Teresa de Haro, Cristina Nevado
Mar 5, 2010·Journal of the American Chemical Society·Daniel W RobbinsJohn F Hartwig
Jun 8, 2011·Beilstein Journal of Organic Chemistry·Jonathan P BrandJérôme Waser
Oct 25, 2011·Chemical Reviews·Yun Shen, Chuan-Feng Chen
Sep 21, 2012·Journal of Medicinal Chemistry·Mahmoud ElkadyStefan A Laufer
Dec 12, 2012·Organic Letters·Youai QiuShengming Ma
Dec 20, 2012·Organic Letters·Gergely L TolnaiJérôme Waser
May 15, 2013·Angewandte Chemie·Yifan LiJérôme Waser
Jan 15, 2014·The Journal of Organic Chemistry·Hua LiuShu-Li You
Jul 10, 2014·Journal of the American Chemical Society·Guoqiang YangJin-Quan Yu

❮ Previous
Next ❯

Citations

Apr 14, 2017·Chemistry : a European Journal·Yifan LiJérôme Waser
Sep 7, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Hossein GhariAlireza Ariafard
Aug 3, 2019·Organic & Biomolecular Chemistry·I F Dempsey HyattCyrus Mowdawalla
Feb 25, 2020·Chemical Communications : Chem Comm·Somsuvra BanerjeeNitin T Patil
Jun 9, 2020·Chemistry, an Asian Journal·Jinkui ChaiNaohiko Yoshikai
Mar 19, 2020·Chemistry : a European Journal·Guillaume PisellaJérôme Waser
Apr 13, 2017·Chemical Communications : Chem Comm·Jing ZhouShengming Ma
Jul 17, 2015·Angewandte Chemie·Johannes Kaschel, Daniel B Werz
Nov 1, 2017·Chemistry, an Asian Journal·Bin WuNaohiko Yoshikai
May 31, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lyubov' N Sobenina, Boris A Trofimov
Jul 1, 2020·Chemistry : a European Journal·Debojyoti Bag, Sanghapal D Sawant
Jan 26, 2021·Beilstein Journal of Organic Chemistry·Daria I TonkoglazovaOlga I Askalepova
Dec 15, 2017·The Journal of Organic Chemistry·Avishek RoyAlakesh Bisai
Nov 30, 2018·Accounts of Chemical Research·Durga Prasad HariJerome Waser

❮ 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.

© 2022 Meta ULC. All rights reserved