Ruthenium-catalyzed C-C coupling of fluorinated alcohols with allenes: dehydrogenation at the energetic limit of β-hydride elimination

Angewandte Chemie
Brannon SamMichael J Krische

Abstract

Ruthenium(II) complexes catalyze the CC coupling of 1,1-disubstituted allenes and fluorinated alcohols to form homoallylic alcohols bearing all-carbon quaternary centers with good to complete levels of diastereoselectivity. Whereas fluorinated alcohols are relatively abundant and tractable, the corresponding aldehydes are often not commercially available because of their instability.

References

Dec 9, 2004·Chemical Reviews·Jun-An Ma, Dominique Cahard
Jul 14, 2005·Chemical Reviews·Shengming Ma
May 27, 2006·Organic & Biomolecular Chemistry·Carla Bobbio, Véronique Gouverneur
Sep 29, 2007·Science·Klaus MüllerFrançois Diederich
Dec 29, 2007·Angewandte Chemie·Vincent A Brunet, David O'Hagan
Mar 26, 2009·Journal of the American Chemical Society·Eduardas SkucasMichael J Krische
Jan 30, 2010·Chemical Society Reviews·Dominique CahardXavier Pannecoucke
Mar 25, 2011·Nature Chemistry·Joseph MoranMichael J Krische
Jan 25, 2012·Angewandte Chemie·Shichao Yu, Shengming Ma
Apr 11, 2012·Angewandte Chemie·Tatiana BessetDominique Cahard
Aug 15, 2012·Angewandte Chemie·Armido Studer
Apr 5, 2013·Chemical Reviews·Ting LuRichard P Hsung
Jul 23, 2013·Angewandte Chemie·Theresa LiangTobias Ritter

❮ Previous
Next ❯

Citations

Jul 28, 2016·Accounts of Chemical Research·Philipp Koschker, Bernhard Breit
Sep 14, 2016·Organic Letters·Yang Xiong, Guozhu Zhang
Jun 23, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Zhanao LvGuochuan Yin
Jun 13, 2017·Angewandte Chemie·Alexander M HaydlMichael J Krische
Jan 30, 2018·Journal of the American Chemical Society·Erica Y TsaiStephen L Buchwald
Mar 1, 2018·Journal of the American Chemical Society·David A PetroneErick M Carreira

❮ 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.