Iron(II)-Catalyzed Site-Selective Functionalization of Unactivated C(sp3 )-H Bonds Guided by Alkoxyl Radicals

Angewandte Chemie
Honghao GuanLei Liu

Abstract

An alkoxyl radical guided strategy for site-selective functionalization of unactivated methylene and methine C-H bonds enabled by an FeII -catalyzed redox process is described. The mild, expeditious, and modular protocol allows efficient remote aliphatic fluorination, chlorination, amination, and alkynylation of structurally and electronically varied primary, secondary, and tertiary hydroperoxides with excellent functional-group tolerance. The application for one-pot 1,4-hydroxyl functionalization of non-oxygenated alkane substrates initiated by aerobic C-H oxygenation is also demonstrated.

References

Oct 25, 1981·Journal of Molecular Biology·M R MurthyM G Rossmann
Jun 1, 2006·Journal of the American Chemical Society·Kami L HullMelanie S Sanford
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
Jun 26, 2008·Angewandte Chemie·Boris Gaspar, Erick M Carreira
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
May 5, 2010·Organic Letters·Rituparna Kundu, Zachary T Ball
Mar 18, 2011·Angewandte Chemie·Timothy Newhouse, Phil S Baran
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 15, 2012·Angewandte Chemie·Steven BloomThomas Lectka
Mar 20, 2013·Journal of the American Chemical Society·Zhaodong LiChaozhong Li
Apr 26, 2013·Angewandte Chemie·Wei Liu, John T Groves
Jul 12, 2013·Beilstein Journal of Organic Chemistry·Pei Chui TooShunsuke Chiba
Aug 21, 2013·Journal of the American Chemical Society·Marie-Gabrielle Braun, Abigail G Doyle
Mar 29, 2014·Angewandte Chemie·Shira D HalperinRobert Britton
Jun 21, 2016·Angewandte Chemie·Julian G WestErik J Sorensen
Sep 28, 2016·Journal of the American Chemical Society·Brian J GroendykeSilas P Cook
Jan 21, 2017·Angewandte Chemie·Xiao-Qiang HuWen-Jing Xiao
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu
Oct 13, 2017·Journal of the American Chemical Society·Dian-Feng ChenTomislav Rovis
Nov 18, 2017·Chemical Science·Desta Doro BumeThomas Lectka
Jan 31, 2018·Journal of the American Chemical Society·Anhua HuZhiwei Zuo

❮ Previous
Next ❯

Citations

Feb 14, 2019·Angewandte Chemie·Robert SzperaVéronique Gouverneur
Oct 11, 2019·Beilstein Journal of Organic Chemistry·Xiaowei LiDayong Shi
Mar 20, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Arnar Guðmundsson, Jan-E Bäckvall
Jul 24, 2020·Angewandte Chemie·Ning JiaoBing Han
Nov 26, 2019·Chemical Science·Franck Le Vaillant, Jérôme Waser
Jul 28, 2019·Chemical Communications : Chem Comm·Xinxin Wu, Chen Zhu
Jan 2, 2021·Chemical Science·Elaine TsuiRobert R Knowles
Jan 23, 2021·Angewandte Chemie·Alexander FawcettJohn F Hartwig
Dec 16, 2019·Chemical Science·Emily N PinterSilas P Cook
Nov 8, 2019·Chemical Science·Melanie A ShortJennifer L Roizen
Jun 8, 2021·Chemical Science·Jayabrata DasDebabrata Maiti
Aug 14, 2021·Chemical Reviews·Xue-Qiang ChuChao-Jun Li
Nov 24, 2020·Organic Letters·Chenyun ShuGangguo Zhu
Aug 30, 2018·Organic Letters·Lin WangArmido Studer
May 20, 2020·Organic Letters·Zhimin XiongGangguo Zhu
Aug 29, 2019·ACS Omega·Andrew S OlsonPatrick H Dussault
Jul 23, 2020·The Journal of Organic Chemistry·Douglas L OrsiRyan A Altman
Jan 31, 2020·Journal of the American Chemical Society·Alastair N HerronJin-Quan Yu
Apr 30, 2020·The Journal of Organic Chemistry·Lei ChenLi Na Guo
Mar 7, 2019·Organic Letters·Hongwei ZhangCuiyu Jiang
Sep 17, 2019·The Journal of Organic Chemistry·Brian J GroendykeSilas P Cook
Jan 26, 2022·Chemical Communications : Chem Comm·Qu-Ping HuFei Pan
Dec 28, 2021·Angewandte Chemie·Nils Lennart FryeArmido Studer

❮ 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.