One-pot two-step dithiocarbamylation of styrenes: metal-free stereoselective synthesis of styrenyl dithiocarbamates

Abstract

Styrene has been functionalized to produce the styrenyl dithiocarbamate by a one-pot two-step procedure without using any metal catalyst. Styrene was transformed into bromo-derivative which undergoes domino nucleophic substitution followed...

Switchable synthesis of 1,4-bridged dihydroisoquinoline-3-ones and isoquinoline-1,3,4-triones through radical oxidation of isoquinolinium salts with phenyliodine(iii) diacetate

“…It is well known that molecular bromine reacts rapidly with alkenes via nucleophilic addition even at lower temperatures (eqn (2)). 13 …”

Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

“…One year later, Saha and Mondal revealed a metal‐free one‐pot two‐step synthesis of trans ‐styryl dithiocarbamates 104 from styrenes 102 and freshly prepared dithiocarbamates 103 through formal C−H dithiocarbamation, using triethylamine as the base and bromine as the mediator (Scheme 30). [126] The reactions were highly stereoselective, providing trans ‐styryl dithiocarbamates as exclusive products. Unlike traditional methods employing Cu‐catalyzed cross‐couplings of styryl bromides or styrylboronic acids, [34,39,51] this method is more straightforward by utilizing readily available styrenes as substrates.…”

“…Moreover, capitalizing on the versatility of the xanthate functional group, a diverse set of CÀ H functionalizations on the branched polyolefins were also unlocked (125)(126)(127)(128)(129)(130), thus enabling the synthesis of an array of advanced materials from commodity polyolefins.…”

A Decade of Advances of CS2/Amines in Three-Component Reactions

“…Banerji and co-workers 2e studied the mild synthesis in an aqueous solution using nanocrystalline MgO as the catalyst. Saha and Mondal 2g developed a catalyst-free, one-pot synthesis of styryl dithiocarbamates. Mechanistically, dibromo intermediate 2.4 is generated in situ by the reaction of the styrene and Br 2 , then 2.4 traps the dithiocarbamic acid intermediate to form 2.5 .…”