PMID: 11312973Apr 21, 2001Paper

Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides

The Journal of Organic Chemistry
M BellerA Tillack

Abstract

Aliphatic and aromatic amines react with 2- and 3-chlorostyrene in the presence of potassium tert-butoxide to give N-substituted 2,3-dihydroindoles in good yields. The combination of this domino-amination protocol with a suitable dehydrogenation reaction gives access to pharmacologically interesting indoles in a one-pot procedure. Overall product yields of N-substituted indoles >50% are obtained by this method starting from commercially available substrates. In addition to the intramolecular base-promoted amination of aromatic C-Cl bonds, metal-free intermolecular aminations of aryl chlorides with primary and secondary amines are described. The use of potassium tert-butoxide as base allows the synthesis of various anilines in good to excellent yields. Due to the formation of aryne intermediates, either N-substituted anilines or meta-substituted anilines are produced with excellent selectivities.

References

Oct 18, 1996·The Journal of Organic Chemistry·Seble Wagaw, Stephen L. Buchwald
Feb 19, 2002·Chemical Reviews·Thomas E. Müller, Matthias Beller

❮ Previous
Next ❯

Citations

May 24, 2006·Chemical Communications : Chem Comm·Patricia Horrillo MartínezFrank Hampel
Feb 24, 2016·Organic Letters·Maayan HirschCharles E Diesendruck
Jun 16, 2016·Organic Letters·Dachuan QiuYang Li
Jun 21, 2016·The Journal of Organic Chemistry·Chriss E McDonaldJustin A Cumens
Apr 27, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gabriele MichelettiCarla Boga
Oct 31, 2014·Organic & Biomolecular Chemistry·Petra DunkelPeter I Dalko
Feb 22, 2017·Chemical Society Reviews·Jiarong ShiYang Li
Aug 27, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Shumiao ZhangHongjian Sun
Oct 26, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chunxia ChenJinsong Peng
Nov 21, 2018·Angewandte Chemie·Martin Pichette DrapeauLukas J Gooßen
Apr 19, 2007·Chemistry, an Asian Journal·Bruce H LipshutzBenjamin R Taft
Oct 8, 2005·Organic & Biomolecular Chemistry·Catherine J SmithJefferson W Tester
Jun 19, 2012·Chemistry : a European Journal·Steffen FleischerMatthias Beller
May 14, 2016·Chemistry, an Asian Journal·Han-Ming ZhangSong Ye
Jan 22, 2014·Organic & Biomolecular Chemistry·Xue-Qi Zhang, Zhong-Xia Wang
Aug 30, 2008·Chemical Reviews·Thomas E MüllerMizuki Tada
May 10, 2003·The Journal of Organic Chemistry·Stéphane CaronYoshinori Murata
Mar 13, 2010·The Journal of Organic Chemistry·Donald C Rogness, Richard C Larock
Sep 19, 2012·Organic Letters·Young Lok ChoiJung-Nyoung Heo
Nov 15, 2012·Organic Letters·Thanh Truong, Olafs Daugulis
Feb 15, 2002·Organic Letters·Artyom Y LebedevAlexander Z Voskoboynikov
Apr 8, 2006·The Journal of Organic Chemistry·Zhijian Liu, Richard C Larock
Nov 24, 2005·Journal of Medicinal Chemistry·Anna QuattropaniMatthias K Schwarz
Nov 25, 2003·Organic Letters·Zhijian Liu, Richard C Larock
Jan 19, 2002·The Journal of Organic Chemistry·Oliver Gaertzen, Stephen L Buchwald
Jan 18, 2005·The Journal of Organic Chemistry·Artyom Y LebedevAlexander Z Voskoboynikov

❮ Previous
Next ❯

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.