N-Bromosuccinimideand Iodine Catalyzed Highly Efficient Deoxygenation ofSulfoxides to Thioethers Using 3-Mercaptopropionic Acid under Mild ReactionConditions

Abstract

A variety of alkyl and aryl sulfoxides have been successfully deoxygenated using 3-mercaptopropionic acid as a reducing agent and a catalytic amount of either NBS or I 2 (5-10 mol%) in MeCN at ambient temperature. Under the described reaction condition, acid sensitive substrates such as acetals remained intact after several hours.

Recent Advances in Aryl Alkyl and Dialkyl Sulfide Synthesis

“…Over the last decades, several sulfur-containing compounds have been transformed into versatile reagents for the synthesis of sulfides [121][122][123][124][125][126][127][128][129][130][131][132]. Trimethylsilyl sulfides (Me 3 SiSR), sulfur, carbon disulfide and thiourea are the most prominent sulfur-containing reagents that were extensively applied for the synthesis of thioethers [133][134].…”

“…acid in the presence of N-bromosuccinimide was utilized as catalytic system for the reduction of sulfoxides (Scheme 51)[124].…”

Indium‐Catalyzed Deoxygenation of Sulfoxides with Hydrosilanes

“…[3] In particular, boranes, [4] which are a representative hydride reagent, have been skillfully applied to achieve deoxygenation. Also, in the presence of an appropriate mediator, magnesium, [5] phosphorus compounds, [6] sulfur compounds, [7] and halides, such as TiI 4 , [8] NaI, [9] and KI 10] behave as effective reducing agents in deoxygenation. Hydrosilane is a mild and easy-handling reagent that has generally shown a high degree of chemoselectivity toward various reducible groups, for decades.…”

N‐Bromosuccinimide Catalyzed One‐pot and Rapid Synthesis of Acetamidobenzyl Naphthols under Mild and Solvent‐free Conditions

“…Herein, we report a new, simple, mild and effective one-pot synthesis of acetamidobenzyl naphthols by the condensation reaction of various benzaldehydes with β-naphthol and acetamide under thermal solvent-free (Method A) and microwave irradiation (Method B) conditions in the presence of N-bromosuccinimide as an effective catalyst (Eq. 1), which has been used as catalyst in some organic reactions, such as dithioacetalization and oxathioacetalization of carbonyl compounds, 21 deoxygenation of sulfoxides to thioethers, 22 conversion of aldehydes to 1,1-diacetates, 23 synthesis of 1,5-benzodiazepine derivatives 24 and acetylation of alcohols. 25…”