Site-Selective Addition of Maleimide to Indole at the C-2 Position: Ru(II)-Catalyzed C-H Activation

Organic Letters
Veeranjaneyulu LankeKandikere Ramaiah Prabhu

Abstract

Synthesis of 3-(indol-2-yl)succinimide derivatives is presented using a directing group strategy. Selective functionalization of C-2 in the presence of highly reactive C-3 in indole derivatives has been achieved. A conjugate addition product instead of Heck-type product has been brought about by careful selection of the alkene partner (maleimides and maleate esters) such that a β-hydride elimination is avoided.

References

Mar 1, 1980·Journal of Medicinal Chemistry·A M CriderK M Yates
Apr 17, 1998·Il Farmaco·V Cechinel FilhoR A Yunes
May 31, 2002·Nature·Jay A Labinger, John E Bercaw
Sep 18, 2002·Accounts of Chemical Research·Barry M Trost
Oct 16, 2002·Accounts of Chemical Research·Fumitoshi Kakiuchi, Shinji Murai
Jul 14, 2005·Chemical Reviews·Sandro Cacchi, Giancarlo Fabrizi
Mar 17, 2006·RNA·Francis RobertJerry Pelletier
Nov 17, 2006·Angewandte Chemie·Rémi MartinezJean-Pierre Genet
Jan 11, 2007·Chemical Reviews·Dino AlbericoMark Lautens
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Apr 13, 2010·Chemical Reviews·Anna J Kochanowska-Karamyan, Mark T Hamann
Mar 11, 2011·Chemical Society Reviews·Lindsay McMurrayMatthew J Gaunt
Jun 15, 2011·Chemical Society Reviews·Joanna Wencel-DelordFrank Glorius
Jul 6, 2011·The Journal of Organic Chemistry·Teh-Chang ChouChun-Hung Wang
Aug 19, 2011·Organic & Biomolecular Chemistry·Luo YangChao-Jun Li
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Jan 18, 2012·Angewandte Chemie·Marius MewaldMartin Oestreich
Mar 7, 2012·Chemical Reviews·Morteza Shiri
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Oct 30, 2013·Organic Letters·Zengqiang SongAndrey P Antonchick
Mar 22, 2014·Journal of the American Chemical Society·Hideya IkemotoMotomu Kanai
Sep 5, 2014·Chemical Communications : Chem Comm·Lingjuan ZhangHuanrong Li
Jan 9, 2015·Chemical Communications : Chem Comm·Xiao-Fei YangTeck-Peng Loh
Feb 18, 2015·Chemistry : a European Journal·Carina SollertLukasz T Pilarski
Sep 9, 2015·Organic Letters·Kiran R BettadapurKandikere Ramaiah Prabhu

❮ Previous
Next ❯

Citations

Jun 18, 2016·The Journal of Organic Chemistry·Puspam KeshriKandikere Ramaiah Prabhu
Aug 30, 2016·Organic Letters·Tomohiro MoritaMasahiro Miura
Apr 25, 2017·Chemical Communications : Chem Comm·Veeranjaneyulu Lanke, Kandikere Ramaiah Prabhu
May 26, 2017·Chemical Communications : Chem Comm·Kiran R BettadapurKandikere Ramaiah Prabhu
Jun 1, 2017·The Journal of Organic Chemistry·Nachimuthu Muniraj, Kandikere Ramaiah Prabhu
Jul 27, 2017·Organic Letters·Shuang-Liang LiuMao-Ping Song
Feb 15, 2018·Chemistry : a European Journal·Guodong ZhangLukas J Gooßen
Sep 20, 2018·Chemical Communications : Chem Comm·Mahadev Sharanappa SherikarKandikere Ramaiah Prabhu
Aug 15, 2018·Angewandte Chemie·Gwilherm Evano, Cédric Theunissen

❮ 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

Beilstein Journal of Organic Chemistry
Huw M L Davies
Accounts of Chemical Research
Michael P Doyle, Karen I Goldberg
Chemical Society Reviews
Huw M L DaviesJin-Quan Yu
Chemical Communications : Chem Comm
Gui-Ling ZhaoArmando Córdova
Journal of Medicinal Chemistry
F D Popp
© 2021 Meta ULC. All rights reserved