Recent advances in PIII -assisted deoxygenative reactions under photochemical or electrochemical conditions

Organic & Biomolecular Chemistry
Xiaoqing ShaoYahui Wang

Abstract

The nucleophilic substitution reactions of hydroxyl groups are one of the most fundamental and widely spread transformations in organic chemistry. Among them, PIII-mediated deoxygenative nucleophilic substitution reactions, such as the Mitsunobu reaction, are frequently used strategies and often require stoichiometric oxidants to activate PIII reagents to induce the desired reactions. It has been illustrated that PIII reagents can be oxidized into the corresponding radical cations through single-electron oxidation by photocatalysis or electro-oxidation. These phosphine radical cations can react with alcohols or carboxylic acids to form the corresponding alkoxyphosphonium or acyloxyphosphonium intermediates, which are very reactive and easily get decomposed. The release of tri-substituted phosphine oxides as a driving force triggers the following nucleophilic substitution. This strategy does not require the use of stoichiometric oxidants and it eludes safety and stability problems. In this review, we summarise the recent advances and discoveries in PIII-assisted direct deoxygenative reactions under photochemical or electrochemical conditions.

References

Dec 13, 2002·Journal of Medicinal Chemistry·J HelfenbeinJ C Madelmont
Dec 8, 2004·Archives of Biochemistry and Biophysics·Laura S Busenlehner, Richard N Armstrong
Sep 8, 2005·Journal of the American Chemical Society·Stephan SchenkErnst Anders
Jul 21, 2006·Organic & Biomolecular Chemistry·Shinro YasuiTetsuro Majima
Jul 27, 2006·Journal of the American Chemical Society·Tracy Yuen Sze But, Patrick H Toy
Sep 25, 2007·Angewandte Chemie·Jens AtzrodtJochen Zimmermann
Apr 23, 2009·Chemical Reviews·K C Kumara SwamyK V P Pavan Kumar
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Oct 1, 2013·Chemical Society Reviews·Jitender Bariwal, Erik Van der Eycken
Mar 4, 2014·Chemical Society Reviews·Carlo SambiagioPatrick C McGowan
Dec 17, 2014·Bioorganic & Medicinal Chemistry Letters·Charles S Elmore, Ryan A Bragg
Aug 21, 2015·Chemical Reviews·Alessandro GandiniEliane Trovatti
Sep 9, 2015·Angewandte Chemie·Joseph A Buonomo, Courtney C Aldrich
Sep 26, 2015·Angewandte Chemie·Giulia BergonziniCarl-Johan Wallentin
Jan 26, 2016·Angewandte Chemie·Liana HieNeil K Garg
Oct 1, 2016·Chemical Reviews·Paula Ruiz-Castillo, Stephen L Buchwald
Oct 30, 2016·The Journal of Organic Chemistry·Sergio Mauricio BonesiAngelo Albini
Dec 22, 2016·Journal of the American Chemical Society·Taoufik Ben HalimaStephen G Newman
Dec 24, 2016·Chemical Society Reviews·Ho Ting LukJavier Pérez-Ramírez
Jul 8, 2017·Chemical Society Reviews·Ryosuke TakiseJunichiro Yamaguchi
Jul 15, 2017·Journal of the American Chemical Society·James A WalkerLevi M Stanley
Sep 2, 2017·Chemical Communications : Chem Comm·Muliang ZhangChengjian Zhu
Oct 13, 2017·Angewandte Chemie·Jens AtzrodtMarc Reid
Oct 5, 2018·Chemical Society Reviews·Javier Urieta-MoraNazario Martín
Oct 12, 2018·Organic & Biomolecular Chemistry·Rhydian H BeddoeRoss M Denton
Oct 24, 2018·Angewandte Chemie·Muliang ZhangJin Xie
Jan 19, 2019·Organic & Biomolecular Chemistry·Xingchao Dai, Feng Shi
Apr 4, 2019·Journal of the American Chemical Society·Shengyang NiPhil S Baran
May 16, 2019·Chemical Society Reviews·Dennis G Hall
Aug 24, 2019·Chemistry : a European Journal·Rehanguli RuziChengjian Zhu

❮ Previous
Next ❯

Citations

Jan 20, 2021·Journal of the American Chemical Society·Jeffrey M LipshultzAlexander T Radosevich

❮ 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.