Pd(II)-catalysed C-H functionalisation of indoles and pyrroles assisted by the removable N-(2-pyridyl)sulfonyl group: C2-alkenylation and dehydrogenative homocoupling

Chemistry : a European Journal
Alfonso García-RubiaJuan Carlos Carretero

Abstract

The easily installed and removed N-(2-pyridyl)sulfonyl group exerts complete C2 regiocontrol over the Pd(II)-catalysed C-H alkenylation of indoles and pyrroles, affording the corresponding products in good isolated yields (typically > or = 70 %). A remarkable feature of this catalyst system is that it tolerates a wide variety of substituted alkenes, including conjugated electron-deficient alkenes, styrenes and 1,3-dienes, as well as conjugated 1,1- and 1,2-disubstituted olefins. The final reductive desulfonylation affords the C2-substituted, free-NH indoles and pyrroles in good yield. This N-(2-pyridyl)sulfonyl-directing strategy has also been extended to the development of a protocol for the intermolecular, dehydrogenative homocoupling of indoles, providing 2,2'-biindoles. Mechanistic work based upon reactions with isotopically labelled starting materials and competitive kinetic studies of electronically varied substrates suggests a chelation-assisted electrophilic aromatic substitution palladation mechanism.

References

Aug 9, 2003·Journal of the American Chemical Society·Eric M Ferreira, Brian M Stoltz
Sep 27, 2003·The Journal of Organic Chemistry·Giorgio AbbiatiCaterina Zoni
Mar 30, 2005·Chemical Communications : Chem Comm·Elena CapitoAlfredo Ricci
May 25, 2005·Angewandte Chemie·Olafs Daugulis, Vladimir G Zaitsev
Jun 2, 2005·Journal of the American Chemical Society·Benjamin S LaneDalibor Sames
Jun 22, 2006·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Aug 17, 2006·Journal of the American Chemical Society·Masabumi TakahashiNobuyuki Tamaoki
Nov 2, 2006·Journal of the American Chemical Society·Stefan J PastineDalibor Sames
Apr 28, 2007·Journal of the American Chemical Society·Domingo García-CuadradoAntonio M Echavarren
May 11, 2007·Organic Letters·Stepan ChuprakovVladimir Gevorgyan
May 26, 2007·Science·David R Stuart, Keith Fagnou
Sep 21, 2007·Journal of the American Chemical Society·David R StuartKeith Fagnou
Nov 9, 2007·Angewandte Chemie·Kyalo Stephen KanyivaTamejiro Hiyama
Feb 6, 2008·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Mar 14, 2008·Angewandte Chemie·Elizabeth M BeckMatthew J Gaunt
May 9, 2008·Organic Letters·Jean-Nicolas DesrosiersAndré B Charette
May 10, 2008·Organic Letters·Gordon BrascheStephen L Buchwald
May 23, 2008·Journal of the American Chemical Society·Timothy A Boebel, John F Hartwig
Jul 11, 2008·Journal of the American Chemical Society·Chris E HouldenKevin I Booker-Milburn
Nov 13, 2008·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Jan 27, 2009·Angewandte Chemie·Chris E HouldenKevin I Booker-Milburn
Feb 28, 2009·Chemistry : a European Journal·Mitsuru MiyasakaMasahiro Miura
Mar 19, 2009·Angewandte Chemie·Marco d'IschiaTadeusz Sarna

❮ Previous
Next ❯

Citations

Jul 20, 2011·Journal of the American Chemical Society·Chunhui HuangVladimir Gevorgyan
Mar 15, 2012·Journal of the American Chemical Society·Anton V GulevichVladimir Gevorgyan
Nov 18, 2011·Acta Crystallographica. Section E, Structure Reports Online·Rui-Bin Hou, Dong-Feng Li
Dec 27, 2011·Acta Crystallographica. Section E, Structure Reports Online·Dong-Feng LiRui-Bin Hou
Dec 5, 2012·Beilstein Journal of Organic Chemistry·Gianluigi BrogginiSilvia Gazzola
Dec 25, 2015·The Journal of Organic Chemistry·Su Jin HanJung Min Joo
Aug 1, 2015·Organic & Biomolecular Chemistry·Ramasamy Manoharan, Masilamani Jeganmohan
Dec 2, 2014·Organic & Biomolecular Chemistry·Shuai-Shuai LiLin Dong
Jun 24, 2017·Chemistry : a European Journal·Marino Petrini
May 1, 2018·Chemistry, an Asian Journal·Hyun Tae KimJung Min Joo
Sep 29, 2011·Angewandte Chemie·Alfonso García-RubiaJuan C Carretero
Jan 15, 2015·ChemSusChem·Tamao IshidaMakoto Tokunaga
Oct 4, 2014·Chemistry : a European Journal·Emil LindbäckKenneth Wärnmark
Jun 5, 2013·Chemistry : a European Journal·Tatsuhiko YoshinoMotomu Kanai
Mar 2, 2011·Chemistry : a European Journal·Alfonso García-RubiaJuan Carlos Carretero
Jul 23, 2013·Angewandte Chemie·Lingkui MengKenichiro Itami
Nov 23, 2013·Organic & Biomolecular Chemistry·Ivan Franzoni, Clément Mazet
Oct 11, 2014·Chemistry : a European Journal·Kevin RouséeChristophe Hoarau
Nov 19, 2011·Chemistry : a European Journal·Cong Wang, Haibo Ge
Apr 15, 2014·Chemistry, an Asian Journal·Chuan LiuShu-Li You
Jan 27, 2011·Angewandte Chemie·Frederic W PatureauFrank Glorius
Aug 1, 2012·Angewandte Chemie·Motoki ToganohHiroyuki Furuta
Nov 20, 2016·Chemistry, an Asian Journal·Bin LiYong-Qiang Wang

❮ 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.