Catalytic domino reaction of ketones/aldehydes with Me3SiCF2Br for the synthesis of α-fluoroenones/α-fluoroenals

Organic Letters
Xiaoning SongMang Wang

Abstract

A unique domino reaction of enolizable carbonyl compounds with Me3SiCF2Br to construct α-fluoroenones and α-fluoroenals is described to undergo the in situ formation of difluorocarbene and silyl enol ether, difluorocyclopropanation, desilylation, ring-opening, and defluorination sequence. In this tandem reaction, Me3SiCF2Br acts as not only the difluorocarbene source but also the TMS transfer agent as well as internal bromide and fluoride anion catalyst. It allows the transformations to occur smoothly under only a catalytic amount of n-Bu4NBr as initiator.

References

Oct 25, 1996·The Journal of Biological Chemistry·M YamashitaT Sakamoto
May 8, 1997·Chemical Reviews·G. K. Surya Prakash, Andrei K. Yudin
Apr 10, 2003·Chemical Reviews·William R Dolbier, Merle A Battiste
Apr 10, 2003·Chemical Reviews·Michał Fedoryński
Jun 5, 2004·The Journal of Organic Chemistry·Xiaohong CaiWilliam R Dolbier
May 20, 2006·The Journal of Organic Chemistry·Guillaume DutheuilXavier Pannecoucke
Jul 1, 2006·American Journal of Physiology. Gastrointestinal and Liver Physiology·Hisayuki UneyamaKunio Torii
Apr 5, 2007·Organic & Biomolecular Chemistry·Samuel Couve-BonnaireXavier Pannecoucke
Oct 2, 2008·The Journal of Organic Chemistry·Xiao-Chun HangJi-Chang Xiao
Apr 14, 2009·The Journal of Organic Chemistry·Arun K GhoshBarbara Zajc
Dec 22, 2009·Chemical Communications : Chem Comm·Jinbo HuFei Wang
Jul 1, 2010·Chemical Communications : Chem Comm·Teresa de Haro, Cristina Nevado
Mar 15, 2011·Chemical Society Reviews·Grégory LandelleJean-François Paquin
Apr 2, 2011·The Journal of Organic Chemistry·William R DolbierWei Xu
Jun 20, 2012·The Journal of Organic Chemistry·Mikhail D KosobokovMarina I Struchkova
Feb 2, 2013·Organic Letters·Vitalij V LevinAlexander D Dilman
Jan 18, 2014·The Journal of Organic Chemistry·Artem A ZemtsovAlexander D Dilman
Feb 21, 2014·Organic Letters·Mikhail D KosobokovAlexander D Dilman
Jun 27, 2014·Organic Letters·Mikhail D KosobokovAlexander D Dilman
Aug 15, 2014·The Journal of Organic Chemistry·Artem V TsymbalAlexander D Dilman
Nov 12, 2014·The Journal of Organic Chemistry·Vladimir O SmirnovAlexander D Dilman
Jan 31, 2015·Organic Letters·Mikhail D KosobokovAlexander D Dilman

❮ Previous
Next ❯

Citations

Aug 25, 2015·The Journal of Organic Chemistry·Vitalij V LevinAlexander D Dilman
Jun 24, 2016·Organic Letters·Alexey L TrifonovAlexander D Dilman
May 26, 2017·Organic Letters·Vyacheslav I SupranovichAlexander D Dilman
Dec 23, 2015·Chemistry : a European Journal·Yuwen ZengJinbo Hu

❮ 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.