Dynamic Covalent Chemistry as a Facile Route to Unusual Main-Group Thiolate Assemblies and Disulfide Hoops and Cages

ChemPlusChem
Ngoc-Minh PhanDarren W Johnson

Abstract

Dynamic Covalent Chemistry (DCC) - combining the robustness of covalent bonds with the self-correcting nature of supramolecular chemistry - facilitates the modular synthesis of complex molecular assemblies in high yields. Although numerous reactions form covalent bonds, only a small set of chemical transformations affect covalent bond formation reversibly under suitable conditions for DCC. Further progress in this area still requires the identification of dynamic motifs and greater insights into their reversibility. We have fruitfully employed DCC of both thiolate coordination to main-group elements and disulfide formation for the facile self-assembly of: (1) metal/metalloid-thiolate assemblies, and (2) purely organic cyclic and caged disulfides, thioethers, and even hydrocarbons, many of which have remained elusive by traditional stepwise synthesis yet form readily through our methods. In this Minireview, we highlight the approaches to prepare these unusual compounds and the factors inducing structural transformations or favoring the formation of certain products over others, given a set of external stimuli or reaction conditions.

References

Mar 5, 2002·The Science of the Total Environment·Uri Dayan, Jean Koch
Dec 20, 2002·Angewandte Chemie·Stuart J RowanJ Fraser Stoddart
Jun 26, 2003·Journal of the American Chemical Society·Sijbren Otto, Stefan Kubik
Jul 19, 2003·Chemistry : a European Journal·Yoshio FurushoToshikazu Takata
Nov 4, 2004·Angewandte Chemie·W Jake VickaryousDarren W Johnson
Jun 23, 2005·Journal of the American Chemical Society·Peter T CorbettSijbren Otto
Sep 30, 2005·Journal of the American Chemical Society·Roberta CacciapagliaLuigi Mandolini
Dec 6, 2005·Inorganic Chemistry·W Jake VickaryousDarren W Johnson
Apr 4, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·James Cookson, Paul D Beer
Sep 21, 2007·Inorganic Chemistry·Virginia M CangelosiDarren W Johnson
Jan 10, 2009·Science·Tracey A Lincoln, Gerald F Joyce
Sep 16, 2009·Chemical Communications : Chem Comm·Virginia M CangelosiDarren W Johnson
Jan 16, 2010·Angewandte Chemie·Virginia M CangelosiDarren W Johnson
Jul 30, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Sean A FontenotDarren W Johnson
Aug 26, 2011·Chemical Reviews·Rajesh ChakrabartyPeter J Stang
May 2, 2012·Journal of the American Chemical Society·Xiao-Ping ZhouChi-Ming Che
Nov 3, 2012·Journal of the American Chemical Society·Fabien B L CougnonJeremy K M Sanders
Jun 19, 2013·Chemical Communications : Chem Comm·Mary S CollinsDarren W Johnson
Nov 10, 2013·Chemical Communications : Chem Comm·Matthew E CarnesDarren W Johnson
Jan 15, 2015·Organic & Biomolecular Chemistry·Fabien B L CougnonJeremy K M Sanders
May 23, 2015·Nature Communications·René-Chris BrachvogelMax von Delius
Apr 5, 2016·Nature Communications·Mary S CollinsDarren W Johnson
Apr 9, 2016·Chemical Communications : Chem Comm·Urs F Fritze, Max von Delius
Apr 12, 2017·Journal of the American Chemical Society·Dávid KomáromySijbren Otto
May 26, 2017·Chemical Communications : Chem Comm·Ivan Aprahamian
Aug 26, 2017·Journal of the American Chemical Society·Hang QuXiaoyu Cao
Sep 30, 2017·Chemistry : a European Journal·Wojciech DrożdżSébastien Ulrich
Feb 2, 2018·Chemistry : a European Journal·Anton D ChavezWilliam R Dichtel
Apr 21, 2018·Chemistry : a European Journal·Szymon SobczakArtur R Stefankiewicz
Nov 19, 2001·Angewandte Chemie·Miguel E Padilla-TostaPaul D Beer
May 3, 2018·Chemical Communications : Chem Comm·Cai-Yun WangHao Li
Nov 15, 2018·Chemical Communications : Chem Comm·Ngoc-Minh PhanDarren W Johnson
Dec 18, 2018·Angewandte Chemie·Tobias H G SchickMichael Mastalerz
May 9, 2019·Chemical Communications : Chem Comm·Yoshiteru KawakamiYoshio Kabe
Aug 29, 2019·Chemistry : a European Journal·Mary S CollinsDarren W Johnson
Sep 14, 2019·Chemical Communications : Chem Comm·Ngoc-Minh PhanDarren W Johnson
May 5, 2020·ChemPlusChem·James E M Lewis, James D Crowley

❮ Previous
Next ❯

Citations

Jan 16, 2021·Chemical Communications : Chem Comm·Daniel CarbajoIgnacio Alfonso
Jan 29, 2021·Chemistry : a European Journal·Szymon SobczakAndrzej Katrusiak
Jul 10, 2021·Organic Letters·Ting-Hsuan ChiangSheng-Hsien Chiu
Sep 2, 2021·JACS Au·Quentin LaurentStefan Matile
Jan 9, 2022·Scientific Reports·Marcin Konopka, Artur R Stefankiewicz

❮ 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.