67592-67-0

Upstream product

• 106-92-3 Allyl glycidyl ether 
• 1666-13-3 diphenyl diselenide 
• 55553-02-1 2-methyl-2-[(prop-2-en-1-yloxy)methyl]oxirane 
• 591-50-4 iodobenzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 185421-44-7 (2,3-Bis-allyloxy-propylselanyl)-benzene 

Relevant academic research and scientific papers

Silver-Catalyzed One-Pot Three-Component Selective Synthesis of β-Hydroxy Selenides

A convenient, multi-component reaction of organoboronic acids, selenium powder and epoxides has been developed, providing an efficient protocol for the synthesis of β-hydroxy selenides with excellent selectivity and good functional group tolerance. Preliminary mechanistic studies suggest that the reaction proceeds through the silver-catalyzed radical selenation of the arylboronic acids to generate a diselenide, and subsequent selenium-mediated selective ring-opening arylselenation of epoxides. (Figure presented.).

Copper-Catalyzed Oxirane-Opening Reaction with Aryl Iodides and Se Powder

Using Se powder as the selenating reagent, the copper-catalyzed double C-Se cross-coupling of aryl iodides, epoxides, and elemental selenium has been developed. This strategy provides a straightforward approach to the synthesis of β-hydroxy phenylselenides with excellent regioselectivity of the ring opening reaction. This process proceeds in generally good yields and is compatible with a broad range of functional groups.

Ultrasound assisted ring-opening reaction of epoxides with 1,2-diphenyldiselenide

Ultrasound assisted ring-opening of epoxides with 1,2-diphenyldiselenide in PEG-400/H2O in the presence of sodium dithionite has been developed, affording β-hydroxy selenides with high regioselectivity in good to excellent yields. Importantly,

Rongalite-promoted odourless and highly regioselective synthesis of β-hydroxyselenides under solvent-free conditions

An efficient and facile procedure for the odourless and highly regioselective synthesis of β-hydroxyselenides by the ring-opening of epoxides with 1,2-diphenyldiselenide in the presence of Rongalite and K2CO3 under solven

One-pot synthesis of β-amino/β-hydroxy selenides and sulfides from aziridines and epoxides

Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a reg

Tetrahydrofuran derivatives from epoxides via group transfer cyclization or reductive radical cyclization of organotellurium and organoselenium intermediates

Monosubstituted epoxides were regiospecifically ring-opened from the sterically least hindered side by benzenetellurolate and benzeneselenolate reagents to afford aryl β-hydroxyalkyl tellurides and selenides, respectively. These materials were O-allylated by treatment with allylic bromides/sodium hydride in tetrahydrofuran and O-prop-2-ynylated when reacted with propargyl bromide/sodium hydride. On photolysis in benzene containing 40 mol % of hexabutylditin, the β-(allyloxy)alkyl aryl tellurides were found to undergo group transfer cyclization to afford 2-substituted 4-[(aryltelluro)methyl]tetrahydrofurans (cis/trans = 1/3-1/10). The aryl β-(prop-2-ynyloxy)alkyl tellurides similarly afforded 2-substituted 4-[(aryltelluro)methylene]tetrahydrofurans with an E/Z-ratio close to unity. The β-(allyloxy)alkyl aryl selenides and aryl β-(prop-2-ynyloxy)alkyl selenides failed to undergo group transfer cyclization. In the presence of tributyltin hydride and 2,2'-azobisisobutyronitrile, the former compounds were found to undergo reductive radical cyclization in high yields to afford 2-substituted 4-methyltetrahydrofurans (cis/trans = 1/3-1/10). Aryl β-(prop-2-ynyloxy)alkyl selenides similarly afforded 2-substituted 4-methylenetetrahydrofurans. 2-Alkoxy-2-(allyloxy)ethyl phenyl selenides, prepared by allyloxyselenenation of vinyl ethers, were found to undergo reductive radical cyclization to afford 2-alkoxy-4-methyltetrahydrofurans (cis/trans = 13-1/4). The preference for formation of trans-2,4-disubstituted tetrahydrofurans in the group transfer and reductive radical cyclizations was rationalized assuming a chairlike transition state with a preferred adoption of a pseudoequatorial position of the 2-substituent. By carrying out the reactions at lower temperatures (ambient or -45°C), using triethylborane as an initiator, it was possible to further increase the trans selectivity in the reductive cyclizations.