Synthesis of vinyl sulfides using glycerol as a recyclable solvent

Lenardão, Eder J.; Silva, Márcio S.; Lara, Renata G.; Marczewski, Júnior M.; Sachini, Maraísa; Jacob, Raquel G.; Alves, Diego; Perin, Gelson

doi:10.3998/ark.5550190.0012.222

Cited by 15 publications

(1 citation statement)

References 9 publications

(12 reference statements)

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“…Lenardão et al 10 have reported an efficient and clean protocol for the hydrothiolation of terminal alkynes which is promoted by potassium fluoride coated alumina (KF/Al 2 O 3 ) in glycerol under MW irradiation. In all cases the anti-Markovnikov adduct was the major product (Scheme 1).…”

Section: Microwave-assisted Chemical Reactions In Glycerolmentioning

confidence: 99%

Glycerol: a solvent and a building block of choice for microwave and ultrasound irradiation procedures

Cintas¹,

Tagliapietra

Gaudino

et al. 2014

Green Chem.

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Glycerol has the potential to be both an excellent renewable solvent in modern chemical processes and a versatile building block in biorefineries. Both of these potential applications may be made easier and more convenient by microwave and/or ultrasound ir radiation. As glycerol is a nontoxic, biodegradable compound, it will provide important environmental benefits to new platform products. Furthermore, significant markets in polymers, polyethers, fuel additives, nanoparticles and other valuable compounds may well be opened up by cutting down the high purification cost of glycerol. The aim of this review is to highlight the best literature examples of glycerol being used, either as solvent or as a reagent, to give interesting results under microwave or ultrasound irradiation.

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Section: Microwave-assisted Chemical Reactions In Glycerolmentioning

confidence: 99%

Glycerol: a solvent and a building block of choice for microwave and ultrasound irradiation procedures

Cintas¹,

Tagliapietra

Gaudino

et al. 2014

Green Chem.

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Access to Sulfides through Free Radical Reaction of Vinyl Halides with Thiols

Shi

Chen

et al. 2019

Asian J Org Chem

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An efficient radical-mediated carbon-sulfur bond formation reaction of vinyl halides with thiols has been developed. This reaction tolerated vinyl chloride substrates, which are barely tolerated in metal-catalyzed reactions, providing vinyl sulfide products. When vinyl iodides were used as substrates, the reactions were regulated by the solvents, yielding vinyl sulfide products in protic solvents (methanol) and alkyl sulfides in aprotic solvents (toluene).[a] Dr. Scheme 1. Examples of the reactions of vinyl halides to form vinyl sulfides.

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Decarbonylation of Salicylaldehyde Activated byp‐Cymene Ruthenium(II) Dimer: Implication for Catalytic Alkyne Hydrothiolation

et al. 2016

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A stoichiometric C–H activation/decarbonylation of salicylaldehyde by [(η6‐p‐cymene)RuCl2]2 gave a carbonyl derivative [(η6‐p‐cymene)RuCl(CO)(Ph‐O)] (1) without the use of CO gas. A variety of polar phosphines were then incorporated into compound 1 to give new RuII cationic catalysts, [(η6‐p‐cymene)Ru(CO)(Ph‐O)L]BF4 (2–8). These were used to catalyse the hydrothiolation of alkynes with a range of thiols in aqueous THF to give anti‐Markovnikov E‐linear vinyl sulfides in high yields.

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Synthesis of vinyl sulfides using glycerol as a recyclable solvent

Cited by 15 publications

References 9 publications

Glycerol: a solvent and a building block of choice for microwave and ultrasound irradiation procedures

Glycerol: a solvent and a building block of choice for microwave and ultrasound irradiation procedures

Access to Sulfides through Free Radical Reaction of Vinyl Halides with Thiols

Decarbonylation of Salicylaldehyde Activated byp‐Cymene Ruthenium(II) Dimer: Implication for Catalytic Alkyne Hydrothiolation

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