32228-17-4

Usage

Chemical class

Benzene derivatives

Structure

Benzene ring with a bromine atom at the 1 position and a thioether group at the 4 position

Thioether attachment

Attached to a phenylethenyl group

Usage

Organic synthesis and chemical research as a starting material or reagent

Applications

Preparation of various organic compounds, pharmaceuticals, agrochemicals, and materials science

Safety

Handle with caution and follow appropriate safety protocols due to potential hazards associated with its chemical structure

Upstream product

• 27691-36-7 Diethyl(4-bromphenylmercapto)-methanphosphonat 
• 100-52-7 benzaldehyde 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 13457-82-4 4-bromothiophenol sodium salt 
• 106-53-6 para-bromobenzenethiol 
• 536-74-3 phenylacetylene 
• 42599-24-6 E-styryl iodide 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 637-44-5 phenylpropyolic acid 
• 27691-35-6 1-bromo-4-[(chloromethyl)sulfanyl]benzene 

Downstream Products

• 32291-79-5 p-Bromphenyl-cis-styrylsulfon 
• 68667-99-2 1-bromo-4-[(E)-2-phenylethenesulfonyl]benzene 

Relevant academic research and scientific papers

Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions

The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.

Zn-catalyzed dihydrosulfenylation of alkynes using thiols

Zinc-catalyzed hydrosulfenylation of alkenes afforded regioselectively the corresponding sulfides in good yields. Furthermore, the method can promote dihydrosulfenylation of alkynes. The procedure could produce anti-Markovnikov type dithioacetals in excellent yields.

Zinc-Catalyzed Synthesis of Dithioacetals through Double Hydrosulfenylation of Alkynes by Thiols

Zinc-catalyzed hydrosulfenylation of alkenes can be performed in various solvents, and the corresponding products are obtained regioselectively. Dihydrosulfenylation of alkynes with thiols can also be achieved by using a zinc catalyst, and the reaction is preferentially promoted over monohydrosulfenylation. The reaction can also give dithioacetals regioselectively in excellent yields.

Hydrothiolation of Alkenes and Alkynes Catalyzed by 3,4-Dimethyl-5-vinylthiazolium iodide and Poly(3,4-dimethyl-5-vinylthiazolium) iodide

The highly selective anti-Markovnikov addition of thiols to unactivated alkenes and alkynes was demonstrated by using 3,4-dimethyl-5-vinylthiazolium iodide or its polymer, poly(3,4-dimethyl-5-vinylthiazolium) iodide, as a complementary catalyst. The reaction proceeded cleanly under base-free conditions in air with both aromatic and aliphatic thiols. The polymer catalyst showed a high turnover number (≈5800) and could be reused up to four times without any loss of catalytic activity. DFT calculations supported stabilization of the thiyl radical intermediate by the thiazolium cation, which resulted in reaction of the radical with unsaturated C?C bonds.

Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex

A practical, efficient, and low-cost heterogeneous catalyst consisting of a Cu-NHC (N-heterocyclic carbene) complex grafted to SBA-15 silica for the catalytic hydrothiolation of alkynes and electron-deficient alkenes under mild reaction conditions has been developed. The heterogeneous catalyst displays higher activity and stereoselectivity to Z-anti-Markovnikov isomers compared with the homogeneous analog under otherwise identical reaction conditions. The catalytic system is applicable to a broad range of alkynes and thiols and is recyclable without significant loss in catalytic performance. High activity and perfect selectivity to alkyl sulfides formed by the addition of electron-deficient alkenes to various thiols catalyzed by the supported Cu-NHC complex were also realized. This journal is the Partner Organisations 2014.

Stereoselective formation of Z- or E-vinyl thioethers from arylthiols and acetylenes under transition-metal-free conditions

Vinyl sulfide formation with good yield and high regio- and stereoselectivities from thiols and acetylenes under transition-metal-free conditions is described. Potassium phosphate was used as an effective additive to enhance the reaction yield and selecti

Indium(iii) catalysed substrate selective hydrothiolation of terminal alkynes

In(OTf)3 is reported as the first catalyst having the ability to selectively catalyse both Markovnikov and anti-Markovnikov hydrothiolation of terminal alkynes under identical reaction conditions depending upon the nature of the thiol employed.

Alkyne hydrothiolation catalyzed by a dichlorobis(aminophosphine) complex of palladium: Selective formation of cis-configured vinyl thioethers

Cis all round: Dichlorobis[1-(dicyclohexylphosphanyl)piperidine]palladium, [(P{(NC5H10)(C6H11) 2})2Pd(Cl)2], is a highly efficient alkyne hydrothiolation catalyst and the first generally applicable system that selectively generates cis-configured anti-Markovnikov adducts in excellent yields within only a few minutes at 120 °C in the presence of only 0.05 mol % of the catalyst (see scheme).

Synthesis of vinyl sulfides by copper-catalyzed decarboxylative C-S cross-coupling

A novel method for the synthesis of vinyl sulfides by the decarboxylative cross-coupling of arylpropiolic acids with thiols using copper(I) salts as catalysts has been developed. In the presence of CuI and Cs2CO 3, a variety of thiols reacted with arylpropiolic acids to afford the corresponding vinyl sulfides in good to excellent yields with high stereoselectivity for Z-isomers.

Recyclable iron/graphite catalyst for c-s cross coupling of thiols with aryl halides under ligand-free conditions

A recyclable iron/graphite (Fe/Cg) catalyst for the efficient C-S cross-coupling of various iodoarenes with aromatic/aliphatic thiols has been developed under ligand-free conditions (26 examples, up to 99% yield). The catalyst can be easily recovered and recycled up to seven cycles without loss of activity. Georg Thieme Verlag Stuttgart.