Transition-metal free synthesis of diaryl vinyl selenides: a simple synthetic approach with high selectivity

Mohan, Balaji; Hwang, Sang Youn; Woo, Hyunje; Park, Kang Hyun

doi:10.1016/j.tet.2014.03.011

Cited by 14 publications

(9 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the other hand, unsymmetrical diaryl vinyl selenides of formula 12 can be prepared in good yields with high selectivity from diaryldiselenides and β‐bromo styrene ( 13 ) employing N,N′‐dimethyl propylene urea as a solvent at 130 °C without the presence of transition‐metals (Scheme 2). The E ‐geometry is the favoured stereoisomer in all cases [66] . Different diaryl diselenides can be used in this free transition metal preparation of diaryl vinyl selenides [66] …”

Section: Chemistrymentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

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.

show abstract

Section: Chemistrymentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…In a continuation of our efforts to develop copper catalysts 29,30 and chalcogen chemistry, 31,32 we report here the efficient use of a copper nanoparticle catalyst in the crosscoupling reaction of an environmentally friendly reagent diphenyl disulfide with terminal alkynes. To investigate the copper nanoparticle-catalyzed alkynylation reaction, diphenyl disulfide (1a) and 1-decyne (2a) were selected as representative substrates for initial screening (Scheme 1).…”

Section: Syn Thesismentioning

confidence: 99%

Copper Nanoparticle Catalyzed Formation of C–S Bonds through Activation of S–S and C–H Bonds: An Easy Route to Alkynyl Sulfides

et al. 2015

Self Cite

View full text Add to dashboard Cite

An efficient method for copper nanoparticle catalyzed ligand-free S-C sp bond formation was developed by using dimethyl sulfoxide as the solvent, a base, and molecular oxygen as a green oxidant. This study provides a new catalytic route for the production of alkynyl sulfides through dual activation of S-S and C-H bonds. A wide range of alkynyl sulfides were synthesized on a large scale with a low catalyst loading (0.5 mol% Cu). This synthetic methodology could also be extended to selenides, whereas tellurides underwent analogous reactions in the absence of a catalyst.

show abstract

“…Interestingly, the related reaction using diphenyl diselenide was ineffectual. Given the time required for the test reaction, we were prompted to utilize the findings from our previous reports on ultrasound irradiation 7 and organochalcogen chemistry 8 to examine activation by physical effects to obtain higher yields of diphenyl tellurides in shorter times. Thus, we surveyed the reactions of diphenyl ditelluride and 4-methoxyphenylboronic acid promoted by conventional heating, microwave, and ultrasound.…”

Section: Figure 1 Some Biologically Active Organotellurium Compoundsmentioning

confidence: 99%

Ultrasound-Assisted, Transition-Metal-Free Synthesis of Diaryl Tellurides from Aryl Boronic Acids: A Possible Free-Radical Mechanism

Mohan

Hwang

Jang

et al. 2014

Synlett

Self Cite

View full text Add to dashboard Cite

The first rapid, catalyst-free synthesis of diphenyl tellurides from readily available diphenyl ditelluride and aryl boronic acids is reported. The high efficiency, general applicability and wide substrate scope, including heterocycles and other functional groups, make this method superior. The technique, which utilizes dimethyl sulfoxide solvent and ultrasound promotion, opens the door for the synthesis of diphenyl tellurides at 100°C in air within a short time in high yields.

show abstract

Transition-metal free synthesis of diaryl vinyl selenides: a simple synthetic approach with high selectivity

Cited by 14 publications

References 24 publications

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Copper Nanoparticle Catalyzed Formation of C–S Bonds through Activation of S–S and C–H Bonds: An Easy Route to Alkynyl Sulfides

Ultrasound-Assisted, Transition-Metal-Free Synthesis of Diaryl Tellurides from Aryl Boronic Acids: A Possible Free-Radical Mechanism

Contact Info

Product

Resources

About

Transition-metal free synthesis of diaryl vinyl selenides: a simple synthetic approach with high selectivity

Cited by 14 publications

References 24 publications

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Copper Nanoparticle Catalyzed Formation of C–S Bonds through Activation of S–S and C–H Bonds: An Easy Route to Alkynyl Sulfides­

Ultrasound-Assisted, Transition-Metal-Free Synthesis of Diaryl Tellurides from Aryl Boronic Acids: A Possible Free-Radical Mechanism

Contact Info

Product

Resources

About

Copper Nanoparticle Catalyzed Formation of C–S Bonds through Activation of S–S and C–H Bonds: An Easy Route to Alkynyl Sulfides