Techniques utilizing photo- and electrochemically induced reactions have been developed to accelerate organic processes. These techniques use light or electrical energy (electron transfer) as a direct energy source without using an initiator or reagent. Thiocyanates are found in biologically active and pharmacological compounds and can be converted into various functional groups. It is one of the most prominent organic scaffolds. Significant development in photo- and electro-chemically induced thiocyanation procedures has been made in recent years for the conception of carbon-sulfur bonds and synthesis of pharmaceutically important molecules. This review discusses different photo- and electro-chemically driven thiocyanation C(sp3)–SCN, C(sp2)–SCN, and C(sp)–SCN bond conception processes that may be useful to green organothiocyanate synthesis. We focus on the synthetic and mechanistic characteristics of organic photo- and electrochemically accelerated C–SCN bond formation thiocyanation reactions to highlight major advances in this novel green and sustainable research field.

/pdf/recent-advances-in-photochemical-and-electrochemically-1rmuv7j4.pdf

Recent advances in photochemical and electrochemically induced thiocyanation: a greener approach for SCN-containing compound formation

Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium-containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium-containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

Organoselenium compounds. Chemistry and applications in organic synthesis.

Imidazo[1,2-a]pyridines are unique nitrogen-containing organic compounds with wide applications in pharmaceuticals, natural products, material science and organometallics. Due to their significant biological and synthetic value, the construction of imidazo[1,2-a]pyridine scaffolds has been a highly intriguing research topic, and substantial progress had been made in the past decades. In this review, we aim to summarize the current advances in direct C–H functionalization of imidazo[1,2-a]pyridines under transition-metal-free conditions. For the selected examples, we focused on the design and catalytic cycle mechanism, as well as on representative outcomes and applications. 

Recent advances in transition-metal-free C–H functionalization of imidazo[1,2-a]pyridines

Anionic species are omnipresent and involved in many important biological processes. A large number of artificial anion receptors has therefore been developed. Some of these are capable of mediating transmembrane transport. However, where transport proteins can respond to stimuli in their surroundings, creation of synthetic receptors with stimuli-responsive functions poses a major challenge. Herein, we give a full overview of the stimulus-controlled anion receptors that have been developed thus far, including their application in membrane transport. In addition to their potential operation as membrane carriers, the use of anion recognition motifs in forming responsive membrane-spanning channels is discussed. With this review article, we intend to increase interest in transmembrane transport among scientists working on host–guest complexes and dynamic functional systems in order to stimulate further developments.

https://pubs.acs.org/doi/pdf/10.1021/acs.chemrev.3c00039

Stimulus-Controlled Anion Binding and Transport by Synthetic Receptors

An efficient NCS-promoted thiocyanation of pyrrolo[1,2-a]quinoxalines with NH4SCN or KSCN is described. A series of diverse 1-thiocyanatopyrrolo[1,2-a]quinoxalines were obtained in good yields with excellent functional group tolerance. With a similar strategy, the selenocyanation of pyrrolo[1,2-a]quinoxalines with KSeCN is also achieved. Importantly, this approach features mild reaction conditions, broad substrate scope, and gram-scale synthesis. Moreover, the transformations of the products are also further examined.

NCS-promoted thiocyanation and selenocyanation of pyrrolo[1,2-a]quinoxalines.

A sustainable and transition metal-free approach for C3 chalcogenation and chalcogenocyanation of imidazopyridines with KXCN (X = S or Se) has been developed under mild conditions. Importantly, thi...

Temperature-Controlled Chalcogenation and Chalcogenocyanation of Imidazopyridines in Water under Transition Metal-Free Conditions.

A Ru(II)-catalyzed bisallylation of imidazopyridines with vinylcyclopropanes or vinyl cyclic carbonate has been successfully realized. Notably, pharmacophore imidazopyridine was utilized as an intrinsic directing group, which gave access to value-added bisallylated products in high yields via double tandem C-H and C-C/C-O activation. The current methodology was featured with broad substrate scope, good functional group compatibility, and operational simplicity.

Ruthenium-Catalyzed C(sp2)-H Bond Bisallylation with Imidazopyridines as Directing Groups.

Photoresponsive molecular tweezer: Control-release of anions and fluorescence switch

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Papers

Temperature-Controlled Chalcogenation and Chalcogenocyanation of Imidazopyridines in Water under Transition Metal-Free Conditions.

Ruthenium-Catalyzed C(sp2)-H Bond Bisallylation with Imidazopyridines as Directing Groups.

Photoresponsive molecular tweezer: Control-release of anions and fluorescence switch