One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions

Organic & Biomolecular Chemistry
Yen-Sen Liao, Chien-Fu Liang

Abstract

In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.

References

Jul 13, 2000·Organic Letters·B L NilssonR T Raines
Sep 8, 2001·Natural Product Reports·J Staunton, K J Weissman
Jul 18, 2002·Chemical Communications : Chem Comm·Shinya IimuraShū Kobayashi
Oct 2, 2003·Chemical Society Reviews·Peter R Schreiner
Nov 25, 2003·The Journal of Organic Chemistry·Derrick L J CliveDon M Coltart
Dec 4, 2004·Organic Letters·Derek Macmillan, David W Anderson
Apr 5, 2008·The Journal of Organic Chemistry·Hong CaoHoward Alper
May 7, 2010·Chemical Communications : Chem Comm·Shinji TanakaMasato Kitamura
May 27, 2010·Chemical Society Reviews·Xiaoqiang ChenJuyoung Yoon
Jun 24, 2010·Organic Letters·Kaname Sasaki, David Crich
Jun 7, 2011·Accounts of Chemical Research·Nicholas A McGrath, Ronald T Raines
Jul 8, 2011·Chemistry : a European Journal·Silja Magens, Bernd Plietker
Nov 1, 2011·Chemical Communications : Chem Comm·Kamala KunchithapathamJames P Stambuli
Jan 10, 2012·Chemical Communications : Chem Comm·Takuya UnoYoshiji Takemoto
Feb 7, 2013·Organic Letters·Mia N BurhardtTroels Skrydstrup
May 25, 2013·Chemical Society Reviews·Caixia YinSidian Li
Jul 13, 2013·Chemistry, an Asian Journal·Hui Liu, Xuefeng Jiang
Mar 15, 2014·Organic Letters·Kelli A Ogawa, Andrew J Boydston
Apr 23, 2014·The Journal of Organic Chemistry·Yu-Ting HuangChin-Fa Lee
Aug 22, 2014·Chemical Reviews·Pankaj ChauhanDieter Enders
Oct 14, 2014·Chemical Society Reviews·Chao ShenXiaogang Liu
Oct 2, 2015·Beilstein Journal of Organic Chemistry·Mohammad Abbasi, Reza Khalifeh
Oct 21, 2015·The Journal of Organic Chemistry·Nagaraju MupparapuQazi Naveed Ahmed
Feb 24, 2017·Journal of the American Chemical Society·Patrick M M SheltonChampak Chatterjee
Apr 19, 2017·Chemical Reviews·Kyle L DunbarChristian Hertweck
Apr 20, 2017·ACS Chemical Neuroscience·Elena SimoniMichela Rosini
May 26, 2017·Nature Communications·Helen M BurkeEoin M Scanlan
Sep 7, 2017·The Journal of Organic Chemistry·Yen-Lin ChouDuen-Ren Hou

❮ Previous
Next ❯

Citations

Sep 6, 2019·Acta Crystallographica. Section C, Structural Chemistry·Jun ZhangXiaopeng Xuan
Dec 11, 2020·The Journal of Organic Chemistry·Shimin XieJianyu Dong

❮ Previous
Next ❯

Methods Mentioned

BETA
column chromatography

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.