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

RSC Advances, Journal Year: 2022, Volume and Issue: 12(10), P. 6214 - 6233

Published: Jan. 1, 2022

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 source without using an initiator reagent. Thiocyanates are found in biologically active pharmacological compounds can be converted into various functional groups. It is one of the most prominent scaffolds. Significant development electro-chemically thiocyanation procedures has made recent years for conception carbon-sulfur bonds synthesis pharmaceutically important molecules. This review discusses different driven C(sp

Language: Английский

---

Photocatalytic C–H Thiocyanation of NH₂-Enaminones and the Tunable Synthetic Routes to 2-Aminothiazoles and 2-Thiazolinones

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 13195 - 13203

Published: Sept. 15, 2022

Visible light photocatalytic reactions of NH2-enaminones and ammonium thiocyanate for chemoselective α-C-H thiocyanation have been realized the first time, providing a sustainable route synthesis thiocyanated NH2-enaminones. In addition, enaminone products can be flexibly transformed into 2-aminothiazoles 2-thiazolinones via simple operation.

Language: Английский

---

Ultrasound-Promoted Synthesis of α-Thiocyanoketones via Enaminone C═C Bond Cleavage and Tunable One-Pot Access to 4-Aryl-2-aminothiazoles

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(12), P. 8248 - 8255

Published: May 26, 2022

Ultrasound has been successfully employed to promote the thiocyanation of C═C bond in enaminones for synthesis α-thiocyanoketones and 2-aminothiazoles. The reactions with ammonium thiocyanate provide ultrasound irradiation at room temperature. More interestingly, simply further heating vessel after ultrasonic leads selective 2-aminothiazoles an unconventional 4-aryl substructure.

Language: Английский

---

Organic Selenocyanates: Rapid Advancements and Applicationsin the Field of Organic Chemistry

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(8)

Published: June 15, 2022

Abstract The incorporation of the cyanato‐chalcogen group (OCN, SCN, and SeCN) has piqued interest many researchers in field modern organic synthetic chemistry. Methodologies for selenocyanation are far less advanced than those OCN SCN chemistry due to scarcity SeCN transfer reagents approaches. It also been discovered that selenocyanate precursor (SeCN) performs significantly better thiocyanate (SCN) terms pharmacological properties scaffolds. Recent years, new (nucleophilic, electrophilic, radical) techniques were introduced allowed creation selenocyanato uncomplicatedly under gentle reaction conditions, particularly transition metal catalysis photo‐/electro‐chemically influenced reactions, which seemingly unimaginable. In this review, we have categorized a variety using various types regents their applications last decades, focusing on multiple catalysts preparation selenocyanates derivatives.

Language: Английский

---

Asymmetric Carbene Insertion into Se‐S Bonds by Synergistic Rh(II)/Guanidine Catalysis Involving Chalcogen‐Bond Assistance

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 2, 2024

The efficient construction of chalcogen-atom-based chiral compounds remains a challenge, despite the importance organoselenium and organosulfur in life materials science. Chalcogen atoms can form net attractive interactions called chalcogen bonds, but it is an undeveloped tool to assist asymmetric catalysis. Herein, we report enantioselective insertion platform install stereogenic center bearing selenyl thiocyano functional groups. Our method operates by synergistic catalysis guanidine achiral dirhodium complex three-component or four-component reaction, through Se-S bond into carbene species, competing successfully with spontaneous racemic process showing high regioselectivity. As elucidated spectroscopic experiments computational studies, unique mechanism involving as well hydrogen bonding was established account for enantiocontrol. stereoselectivity holds broad array selenylthiocyanatopropanoates, which showed excellent anti-inflammatory toward IL-1β low cytotoxicity.

Language: Английский

---

Photoinduced Synthesis of Thiocyanates through Hydrogen Atom Transfer and One-Pot Derivatization to Isothiocyanates

Organic Letters, Journal Year: 2022, Volume and Issue: 24(40), P. 7366 - 7371

Published: Oct. 4, 2022

Photoinduced benzylic C–H thiocyanation is described. A series of alkyl thiocyanates were efficiently obtained by using Selectfluor as the oxidant. Moreover, we accomplished one-pot isothiocyanation following thiocyanation. The and isothiocyanates applied to divergent transformation pharmaceuticals.

Language: Английский

---

Electrochemical oxidative regio- and stereo-selective thio(seleno)cyanation of enamides and mechanistic insights

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(17), P. 6556 - 6561

Published: Jan. 1, 2022

An electrochemical oxidative thio(seleno)cyanation of enamides to synthesize various ( E )-β-thio(seleno)cyanated enamide compounds is reported herein.

Language: Английский

---

Regioselective C–H Thiocyanation of Arenes by Iron(III) Chloride Catalysis

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7208 - 7218

Published: May 9, 2023

Aryl thiocyanates are flexible synthetic intermediates that can be used in the preparation of a diverse range arene building blocks for medicinal chemistry. Here, we report fast and efficient Lewis acid-catalyzed method regioselective thiocyanation arenes. Iron(III) chloride was found to an effective acid activation N-thiocyanatosaccharin subsequent wide activated The procedure applicable biologically active compounds such as metaxalone estradiol derivative part one-pot tandem iron-catalytic process regioselective, dual functionalization block.

Language: Английский

---

Introducing Alkyl Selenocyanates as Bifunctional Reagents in Photoredox Catalysis: Divergent Access to Ambident Isomers of −SeCN

Organic Letters, Journal Year: 2024, Volume and Issue: 26(40), P. 8447 - 8452

Published: Aug. 22, 2024

Owing to their diverse biological activities and versatility as synthetic precursors, organoselonocyanes categorize themselves vital compounds. However, a limited reagent pool restricts utility. In the present work, alkyl selenocyanates are hereby established new bifunctional reagents for simultaneous transfer of an group in addition −SeCN. These reagents, when merged with photocatalysis, provide key accessing organoselenocyanates from feedstock olefins efficient atom-economic fashion. A route analogous isoselenocyanate isomers facilitated by Lewis acid catalysis is also reported, presenting divergent strategy both ambident −SeCN manner.

Language: Английский

---

Transition metal catalysed direct sulfanylation of unreactive C–H bonds: an overview of the last two decades

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(31), P. 6072 - 6177

Published: Jan. 1, 2022

Transition metal catalysed C–S bond formation from unreactive C–H bonds is a remarkable tool in the late-stage functionalization of complex molecules. This review highlights significant advances and mechanistic analyses last two decades.

Language: Английский

---