An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

Chemistry : a European Journal
Bo RenHai Dong

Abstract

In this study, [Fe(dibm)3 ] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

References

Aug 26, 1998·Advances in Carbohydrate Chemistry and Biochemistry·T B Grindley
Feb 20, 2003·Journal of the American Chemical Society·Yoshihiro MatsumuraOsamu Onomura
Jul 13, 2004·Brain Research. Developmental Brain Research·Scott M JenkinsStanley Barone
Apr 20, 2007·Nature·Cheng-Chung WangShang-Cheng Hung
Jul 1, 2008·Accounts of Chemical Research·Benjamin D Sherry, Alois Fürstner
Sep 24, 2009·Chemical Reviews·Moriah Sandy, Alison Butler
Jan 6, 2011·Chemical Communications : Chem Comm·Yann BourdreuxJean-Marie Beau
Mar 2, 2011·Journal of the American Chemical Society·Doris Lee, Mark S Taylor
Dec 14, 2011·Angewandte Chemie·Stefanie A CantalupoLinda H Doerrer
Jan 31, 2012·The Journal of Organic Chemistry·Hai DongOlof Ramström
Apr 25, 2012·Chemical Communications : Chem Comm·Yixuan ZhouHai Dong
Dec 12, 2012·Organic & Biomolecular Chemistry·Hai DongOlof Ramström
Oct 30, 2013·The Journal of Organic Chemistry·Yixuan ZhouHai Dong
Nov 28, 2013·Organic Letters·C Liana Allen, Scott J Miller
Jan 31, 2014·Journal of the American Chemical Society·Danyang ZhuJianglong Zhu
Mar 13, 2014·Chemistry, an Asian Journal·Bo RenOlof Ramström
Mar 14, 2014·Chemistry : a European Journal·I-Hon ChenVy M Dong
Feb 3, 2015·The Journal of Organic Chemistry·Lei WangTodd L Lowary
Feb 11, 2015·Accounts of Chemical Research·Samuel J DanishefskyChi-Huey Wong
Feb 11, 2015·The Journal of Organic Chemistry·Simiao LuT Bruce Grindley
Mar 10, 2015·Chemical Reviews·Ingmar Bauer, Hans-Joachim Knölker
May 1, 2015·Organic Letters·Satsawat VisansirikulAlexei V Demchenko
May 9, 2015·Organic Letters·Shu-Lun Tang, Nicola L B Pohl

❮ Previous
Next ❯

Citations

Apr 23, 2016·Journal of the American Chemical Society·Peng PengRichard R Schmidt
Mar 1, 2017·Chemical Communications : Chem Comm·My Linh TongStefan F Kirsch
May 3, 2019·Organic & Biomolecular Chemistry·Tinghua Wang, Alexei V Demchenko
Aug 9, 2019·Chemistry : a European Journal·Satoru KuwanoTakayoshi Arai
Mar 31, 2019·Carbohydrate Research·Timothé VuckoSandrine Lamandé-Langle
Jul 21, 2021·Organic Letters·Jérôme AlsarrafAndré Pichette
Jun 6, 2018·Chemical Reviews·Suvarn S KulkarniShang-Cheng Hung
Dec 4, 2019·Journal of the American Chemical Society·Yan-Long JiangZhen Yang
Dec 7, 2018·Chemical Reviews·Victoria Dimakos, Mark S Taylor

❮ 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.