Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis

Angewandte Chemie
Jack TwiltonDavid W C MacMillan

Abstract

The combination of nickel metallaphotoredox catalysis, hydrogen atom transfer catalysis, and a Lewis acid activation mode, has led to the development of an arylation method for the selective functionalization of alcohol α-hydroxy C-H bonds. This approach employs zinc-mediated alcohol deprotonation to activate α-hydroxy C-H bonds while simultaneously suppressing C-O bond formation by inhibiting the formation of nickel alkoxide species. The use of Zn-based Lewis acids also deactivates other hydridic bonds such as α-amino and α-oxy C-H bonds. This approach facilitates rapid access to benzylic alcohols, an important motif in drug discovery. A 3-step synthesis of the drug Prozac exemplifies the utility of this new method.

References

Jul 12, 1996·The Journal of Organic Chemistry·Wei-Zhong Liu, Frederick G. Bordwell
Oct 25, 2001·Journal of the American Chemical Society·K E TorracaS L Buchwald
Nov 4, 2011·Journal of the American Chemical Society·Dipannita KalyaniMelanie S Sanford
Apr 10, 2013·Journal of the American Chemical Society·Basudev SahooFrank Glorius
May 3, 2013·Journal of Cardiovascular Pharmacology and Therapeutics·William H Frishman
Apr 16, 2014·Journal of the American Chemical Society·Xing-zhong ShuF Dean Toste
Aug 13, 2015·Nature·Jack A TerrettDavid W C MacMillan
Oct 7, 2015·Journal of the American Chemical Society·Melissa Lee, Melanie S Sanford
Nov 5, 2015·Journal of the American Chemical Society·Jennifer M HowellM Christina White
Apr 26, 2016·Chemical Reviews·Kazimer L SkubiTehshik P Yoon
Jun 25, 2016·Science·Emily B CorcoranDavid W C MacMillan
Aug 2, 2016·The Journal of Organic Chemistry·Megan H ShawDavid W C MacMillan
Sep 1, 2016·Inorganic Chemistry·Kasper P Kepp
Feb 9, 2017·Journal of the American Chemical Society·Wasim M AkhtarTimothy J Donohoe
Jun 22, 2017·Nature·Chip LeDavid W C MacMillan
Nov 28, 2017·The Journal of Organic Chemistry·Rauful Alam, Gary A Molander
Oct 1, 1995·Human Psychopharmacology·S J Van den Berg

❮ Previous
Next ❯

Citations

Nov 11, 2018·Chemistry : a European Journal·Qing XiaQingmin Wang
Oct 9, 2018·Angewandte Chemie·Samantha RoheLouis Barriault
Oct 7, 2018·Angewandte Chemie·John A MilliganGary A Molander
Aug 1, 2018·Angewandte Chemie·Mikhail A SyroeshkinIgor V Alabugin
May 9, 2019·Organic & Biomolecular Chemistry·Yating Zhao, Wujiong Xia
Aug 2, 2019·Angewandte Chemie·Jompol ThongpaenOlivier Baslé
May 23, 2019·Angewandte Chemie·Dirk Leifert, Armido Studer
Jan 11, 2020·Chemistry : a European Journal·Sk Sheriff ShahN D Pradeep Singh
Sep 2, 2020·Chemical Communications : Chem Comm·Jing LiuWen-Jing Xiao
Sep 22, 2020·Beilstein Journal of Organic Chemistry·Shahboz Yakubov, Joshua P Barham
Jun 27, 2019·Angewandte Chemie·Andrés García-DomínguezCristina Nevado
Aug 9, 2020·Beilstein Journal of Organic Chemistry·Lucas Guillemard, Joanna Wencel-Delord
Jan 30, 2019·Nature Communications·Linbin NiuAiwen Lei
Jun 10, 2020·Chemistry : a European Journal·Pradeep SinghN D Pradeep Singh
Nov 24, 2020·Organic & Biomolecular Chemistry·Mandapati Bhargava ReddyRamasamy Anandhan
Jan 30, 2021·Accounts of Chemical Research·Stavros K Kariofillis, Abigail G Doyle
Feb 23, 2021·Chemical Communications : Chem Comm·Yan-Long Zheng, Stephen G Newman
Apr 29, 2021·Organic & Biomolecular Chemistry·Andrea GualandiPier Giorgio Cozzi
Jun 12, 2021·The Journal of Organic Chemistry·Bruno LainerPaweł Dydio
Jun 15, 2021·Chemical Science·Mirjam R SchreierOliver S Wenger
Mar 18, 2020·Journal of the American Chemical Society·Qing AnZhiwei Zuo
Mar 23, 2019·Journal of the American Chemical Society·Victoria DimakosMark S Taylor
Feb 15, 2020·Journal of the American Chemical Society·Hiromu FuseMotomu Kanai
Aug 14, 2020·Journal of the American Chemical Society·Feng Zhu, Maciej A Walczak
Apr 16, 2019·Journal of the American Chemical Society·Thomas VerheyenStephen G Newman
Oct 27, 2018·Journal of the American Chemical Society·Pin XiaoWalter Thiel
Apr 4, 2020·The Journal of Organic Chemistry·Joan InoaYalan Xing
Sep 4, 2021·Journal of the American Chemical Society·Eric S IsbrandtStephen G Newman

❮ 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.