Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines

Organic Letters
Yibin YeGavin Chit Tsui

Abstract

A new method for the synthesis of 2-(trifluoromethyl)indoles using easily accessible 2-alkynylanilines and a well-established fluoroform-derived CuCF3 reagent is described. This method utilizes a domino trifluoromethylation/cyclization strategy to construct the indole cores with no ambiguity of the CF3 position. The intriguing 3-formyl-2-(trifluoromethyl)indoles can also be synthesized by this protocol, which are useful intermediates for the preparation of trifluoromethylated drug analogues. The ultimate CF3 source is the inexpensive industrial byproduct fluoroform.

References

Jul 14, 2006·Chemical Reviews·Guy R Humphrey, Jeffrey T Kuethe
Feb 15, 2007·International Journal of Clinical Practice·A Altun, B Ugur-Altun
Dec 1, 2009·Angewandte Chemie·Marco Bandini, Astrid Eichholzer
Jan 18, 2011·The Journal of Organic Chemistry·Todd D SenecalStephen L Buchwald
Mar 8, 2011·Chemical Communications : Chem Comm·Jun XuLei Liu
Apr 21, 2011·Chemistry : a European Journal·Xin MuGuosheng Liu
Jul 23, 2011·Organic & Biomolecular Chemistry·Rubén Vicente
Aug 17, 2011·Proceedings of the National Academy of Sciences of the United States of America·Yining JiPhil S Baran
Dec 6, 2011·Journal of the American Chemical Society·Alessandro ZanardiVladimir V Grushin
Dec 8, 2011·Journal of the American Chemical Society·Lingling Chu, Feng-Ling Qing
Dec 14, 2011·Nature·David A Nagib, David W C MacMillan
Feb 23, 2013·Chemical Communications : Chem Comm·Yang LiMatthias Beller
Jun 6, 2013·Chemical Communications : Chem Comm·Sangwon SeoMichael F Greaney
Nov 10, 2013·Beilstein Journal of Organic Chemistry·Jie HuNan Zheng
Nov 21, 2013·The Journal of Organic Chemistry·Marc PressetGary A Molander
Feb 4, 2014·Current Topics in Medicinal Chemistry·Andrei A Gakh, Yuriy Shermolovich
Feb 6, 2014·Organic Letters·Bo Zhang, Armido Studer
Mar 14, 2014·Organic Letters·Michael G MorminoJohn F Hartwig
Jan 23, 2015·Chemistry : a European Journal·Romain Rey-RodriguezIsabelle Gillaizeau
Jan 31, 2015·Chemical Reviews·Concepción AlonsoFrancisco Palacios
Apr 25, 2015·Chemistry : a European Journal·Yuanzheng ChengShouyun Yu
Aug 11, 2015·Nature Communications·Joel W BeattyCorey R J Stephenson
Jan 11, 2016·Angewandte Chemie·Edon VitakuJon T Njardarson
Jan 26, 2016·Angewandte Chemie·Kishore NatteMatthias Beller
May 4, 2016·Journal of the American Chemical Society·Lu LiChao-Jun Li
May 24, 2016·Angewandte Chemie·Johannes MorsteinJohn F Hartwig

❮ Previous
Next ❯

Citations

May 24, 2019·Angewandte Chemie·Jia-Xiang XiangFeng-Ling Qing

❮ 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.