15642-77-0

Upstream product

• 922-67-8 propynoic acid methyl ester 
• 645-96-5 Benzeneselenol 
• 1111071-92-1 phenylselenyl zinc chloride 
• 29680-62-4 Tris(phenylseleno)borane 

Relevant academic research and scientific papers

Chemoselective and metal-free reduction of α,β-unsaturated ketones by: In situ produced benzeneselenol from O -(tert -butyl) Se-phenyl selenocarbonate

The carbon-carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use of toxic Se/CO mixture and NaSeH, or the smelly and air-sensitive benzeneselenol, is avoided. This journal is

O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol

A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.

"On-water" Michael-type addition reactions promoted by PhSeZnCl

In this communication we report that our reagent PhSeZnCl can be conveniently used to effect Michael addition like reactions of unsaturated ketones and electron-deficient alkynes, leading to synthetically useful β-seleno derivativesand vinyl selenides, respectively. The reactions are effected at room temperature in THF as well as under "on water" conditions. When the addition occurs on a triple bond, good stereoselectivity is observed, and the reaction shows a rate acceleration in water suspension. Copyright

Palladium and platinum catalyzed hydroselenation of alkynes: Se-H vs Se-Se addition to C≡C bond

A mechanistic study of the hydroselenation of alkynes catalyzed by Pd(PPh3)4 and Pt(PPh3)4 has shown that the palladium complex gives products of both Se-H and Se-Se bond addition to the triple bond of alkynes, while the platinum complex selectively catalyzes Se-H bond addition. The key intermediate of PhSeH addition to the metal center, namely Pt(H)(SePh)(PPh3)2, was detected by 1H-NMR spectroscopy. The analogous palladium complex rapidly decomposes with evolution of molecular hydrogen. A convenient method was developed for the preparation of Markovnikov hydroselenation products H2C=C(SePh)R, and the scope of this reaction was investigated. The first X-ray structure of the Markovnikov product H2C=C(SePh)CH2N+ HMe2·HOOC=COO- is reported.

Mechanism of catalytic addition of benzeneselenol to alkynes

Addition of benzeneselenol to terminal alkynes HC≡CR, catalyzed by Pd(0) complexes, leads to formation of mixtures of mono- and bis(phenylseleno)alkenes, depending on the nature of the R substituent. Electron-donor groups (R = Bu, CH2OH, CH2NMe2) give rise to addition according to the Markownikoff rule, whereas from alkynes with electron-acceptor groups (R = Ph, COOMe) mixtures of products are formed as a result of side reactions. A probable reaction mechanism includes oxidative addition of benzeneselenol to the metal, alkyne insertion into the Pd-Se bond, and reductive elimination.

Versatile Cyclisation Reactions Using Selenoboranes

Tris(phenylseleno)borane and tris(methylseleno)borane reacted with terminal acetylenes to afford (Z)-vinyl selenides.This reaction was initiated by oxygen and the intermediates were vinyl radicals.This radical reaction could be applied to the intramolecular free radical cyclisation of enynes and some heterocycles and carbocycles were synthesised.This novel method could be also employed in the synthesis of α-kainoid derivatives.

VINYL RADICAL GENERATION WITH SELENOBORANE AND ITS APPLICATION TO CYCLIZATION REACTION OF ENYNES

Tris(methylseleno)- and tris(phenylseleno)boranes added to acetylenes to afford methylseleno- and phenylseleno-substituted Z-vinylselenides in high yields.The addition reactions proceeded by way of free radicals and were applied to cyclization reactions o