129053-37-8

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 71098-88-9 N-phenylselanylphthalimide 
• 1666-13-3 diphenyl diselenide 
• 129803-02-7 benzeneselenyl fluoride 

Downstream Products

• 14251-62-8 (Z)-α-fluoro-β-methylstyrene 

Relevant academic research and scientific papers

PhSeOTf-Et3N·3HF and PhSeSbF6-Et3N·3HF as new PhSe-F equivalents in the fluoroselenenylation of actylenes

The novel reagents PhSeOTf-Et3N·3HF and PhSeSbF6-Et3N·3HF act as PhSe-F equivalents in the fluoroselenenylation of alkynes. Oct-4-yne, cycloundecyne and cyclododecyne, as well as the unsymmetrical alkynes Ph-C≡C-Me and Bu-C≡C-R (R = Me, Et, iPr and tBu) give the corresponding (E)-fluoro(phenylseleno)alkenes in preparative yields. The reagent PhSeOTf-Et3N·3HF gives a similar product composition of regioisomers to Ph2Se2-XeF2 in addition reactions to Bu-C≡C-R. This is indicative of a similar reaction mechanism of the reagents. Probably a selenirenium ion acts as an intermediate. X-Ray single crystal structure analysis of (E)-1-fluoro-2-phenylselenocycloundecene confirms the trans-addition of [PhSe-F] to cycloundecyne.

Phenylselenofluorination of alkenes and alkynes promoted by difluoroiodotoluene and diphenyldiselenide

The oxidation of diphenyldiselenide with 4-iodotoluene difluoride (DFIT) in dichloromethane produces in situ an efficient phenylselenofluorinating agent of alkenes and internal alkynes.

13C, 19F and 77Se NMR study of vicinal (E)-fluoro(organylseleno)olefins and [(E)-fluoroalkenyl]diorganylselenonium salts

13C, 19F and 77Se NMR spectra of the (E)-fluoro(organylseleno)olefins R1(F)Cα=CβR2(SeR3) and the [(E)-fluoroalkenyl]diorganylselenonium salts R1(F)Cα/

Electrochemical Fluoro-Chalcogenation

Electrochemical fluoro-chalcogenation (S, Se) of alkenes and alkynes, and recycle use of in situ generated PhSeF for allylic fluorination are discussed.

Fluoroselenylation of acetylenes with xenon difluoride-diorganyl diselenides and xenon difluoride-phenylseleno(trialkyl)silanes

A new, efficient method of fluoroselenenylation of terminal, and open-chain symmetric and unsymmetric disubstituted acetylenes and cycloalkynes, gives vicinal (E)-fluoroalkenyl selenides in moderate to high yields by addition of selenenyl fluoride equivalents. These are formed in situ from xenon difluoride and diaryl, dibenzyl or primary and secondary dialkyl diselenides. Alternatively, the benzeneselenenyl fluoride equivalent is formed by treatment of more reactive phenylselenotrialkylsilanes with xenon difluoride. The regiochemistry of the addition is strongly dependent on the steric effects of substituents bonded to the acetylene.

Phenylthio (and phenylseleno)fluorination of alkenes and alkynes using N-phenylthio (and phenylseleno)phthalimide combined with pyridine*9HF or Et3N*3HF complexes

N-Phenylthiophthalimide and N-phenylselenophthalimide combined with pyridine*9HF or Et3N*3HF complexes allow the formal addition of elements of PHSF or PhSeF across the carbon-carbon double or triple bond by a one-pot reaction.Pyridine*9HF, a strongly aci

Phenylselenofluoration d'alcynes

The electrophilic anti-addition of the elements of benzeneselenenyl fluoride towards carbone-carbone triple bonds is performed by a one-pot reaction of N-phenylselenophthalimide and triethylamine tris-hydrofluoride with disubstituted alkynes ; starting from monosubstituted alkynes, the reaction proceeds further to afford vinylic diselenated compounds after hydrofluoric acid elimination. Some products of mono-addition could be transformed into vinylic or allenic fluorides.