A calcium-mediated three-component selenylation of -difluoroalkenes using alcohols as nucleophiles and -(phenylseleno)phthalimide as the selenylation agent has been developed for the efficient synthesis of various α,α-difluoroalkyl-β-selenides. This selenylation reaction exhibits broad substrate and functional group tolerance, along with high levels of chemo- and regioselectivity. Additionally, the synthetic utility of the developed transformation in the late-stage functionalization of drug molecules was demonstrated.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c02360 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Calcium(II)-Mediated Three-Component Selenylation of -Difluoroalkenes: Access to α,α-Difluoroalkyl-β-selenides.
Org Lett
July 2024
Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences and The Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, Guangdong 511436, China.
A calcium-mediated three-component selenylation of -difluoroalkenes using alcohols as nucleophiles and -(phenylseleno)phthalimide as the selenylation agent has been developed for the efficient synthesis of various α,α-difluoroalkyl-β-selenides. This selenylation reaction exhibits broad substrate and functional group tolerance, along with high levels of chemo- and regioselectivity. Additionally, the synthetic utility of the developed transformation in the late-stage functionalization of drug molecules was demonstrated.
View Article and Find Full Text PDFIodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium.
Molecules
September 2022
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
A one-pot synthesis of linear and cyclic β-alkoxyselenides is developed through the iodine-mediated three-component reaction of elemental selenium with alkenes (dienes) and alcohols. Selenylation of 1,5-hexadiene gives 2,5-di(methoxymethyl)tetrahydroselenophene and 2-methoxy-6-(methoxymethyl)tetrahydro-2-selenopyran via the 5 and 6- cyclization. 1,7-Octadiene affords only linear 1:2 adduct with two terminal double bonds.
View Article and Find Full Text PDFSynthesis of Selenyl-Substituted Quinoline Derivatives via Substrate-Controlled Three-Component Domino Reactions.
J Org Chem
September 2022
Pharmacy School, Guilin Medical University, Guilin 541004, People's Republic of China.
A simple and efficient method for the preparation of selenyl-substituted quinoline derivatives through a C-H selenylation of in situ-generated 3-acetyl quinoline has been developed. This protocol is easy to handle, scalable, and good functional group tolerant, providing a rapid method to 3-selenoacetyl quinoline and 3-diselenoacetyl quinoline derivatives.
View Article and Find Full Text PDFTransition-metal-catalyzed one-pot selenylation of electrophilic arylating agents using triphenyltin chloride/Se as a phenylselenating agent.
Org Biomol Chem
June 2022
Department of Chemistry, Faculty of Science, University of Kurdistan, 66177-15175, Sanandaj, Iran.
Three novel and efficient protocols for the synthesis of phenyl aryl selenides through a three-component coupling reaction of triphenyltin chloride with aryl halides, phenolic esters or nitroarenes, and Se powder catalyzed by CuI or Cu(OAc) in the presence of a base in PEG200 at 90-100 °C have been developed. Also, NiFeO as a magnetically reusable nanocatalyst was applied in these reactions under similar reaction conditions. The present methods are superior to other currently available methods due to the use of triphenyltin chloride/Se as a phenylselenating agent and phenolic esters and nitroarenes as a coupling partner for C-Se-C bond formation for the first time, a green solvent and inexpensive and reusable catalysts, and avoidance of any toxic and expensive arylselenating reagents.
View Article and Find Full Text PDFVisible Light-Mediated C(sp)-H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst.
J Org Chem
January 2022
Department of Chemistry, Indian Institute of Technology Patna, Bihta, Patna 801103, India.
Herein, we report an efficient methodology for the synthesis of alkyl, benzyl, and phenyl selenoethers of aminopyrazoles and aminouracils by C(sp)-H functionalization in the presence of visible light and Rose Bengal as an organophotocatalyst. The reaction of amino pyrazole/iosothiazole/isoxazole or amino uracils with 0.5 equivalent of diphenyl/dibenzyl/diethyl diselenides in the presence of visible light in acetonitrile medium and a catalytic amount of Rose Bengal provided the corresponding phenyl, benzyl, or ethyl selenoethers in good to very good yields.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!