65234-92-6Relevant academic research and scientific papers
Time-economical synthesis of selenofunctionalized heterocycles via I2O5-mediated selenylative heterocyclization
Zhou, Chen-Fan,Zhang, Yun-Qian,Ling, Yong,Ming, Liang,Xi, Xia,Liu, Gong-Qing,Zhang, Yanan
supporting information, p. 420 - 426 (2022/01/20)
A time-economical and robust synthesis of various selenofunctionalized heterocycles was accomplished via I2O5-mediated selenocyclizations of olefins with diselenides. Using this method, 116 selenomethyl-substituted heterocycles were
Preparation of selenofunctionalized heterocycles via iodosobenzene-mediated intramolecular selenocyclizations of olefins with diselenides
Wang, Peng-Fei,Yi, Wei,Ling, Yong,Ming, Liang,Liu, Gong-Qing,Zhao, Yu
supporting information, p. 2587 - 2591 (2021/03/15)
An intramolecular selenocyclizations of olefins mediated by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provided access to a wide range of selenenylated heterocycles under ambient conditions. The striking advantages of this protocol over all previous methods include mild reaction conditions, easy operation, good yields, high levels of functional group compatibility, large–scale application and suitability for the late-stage functionalization of complex molecules of biological importance.
Iodine-mediated acyloxyselenenylation of alkenes
Wang, Xiaolong,Wang, Junxing,Li, Hongjie,Yan, Jie,Yang, Zhenping
, p. 2745 - 2752 (2018/08/23)
In the presence of I2, an acyloxyselenenylation of alkenes with diselenides and carboxylic acids is developed. This metal-free iodine-mediated acyloxyselenenylation proceeds efficiently under mild reaction conditions, affording a series of 2-acyloxy-1-selenides with high regioselectivity and in moderate to good yields.
The Binary Reagent PhSeSePh-CuOTf: a Useful Phenylselenylating Agent
Miyachi, Nobuhide,Satoh, Hisao,Shibasaki, Masakatsu
, p. 2049 - 2050 (2007/10/02)
The binary reagent PhSeSePh-CuOTf has been found to be useful for the conversion of alkynyltrimethylsilanes into 1-phenylselenoalk-1-ynes as well as for phenylselenolactonization and phenylselenoetherification.
Ring-Closure Reactions Initiated by the Peroxydisulfate Ion Oxidation of Diphenyl Diselenide
Tiecco, M.,Testaferri, L.,Tingoli, M.,Bartoli, D.,Balducci, R.
, p. 429 - 434 (2007/10/02)
The oxidation of diphenyl diselenide with ammonium peroxydisulfate proceeded cleanly to afford phenylselenium cations and sulfate anions.This is a very simple and efficient method to produce phenylselenium cations in the absence of nucleophilic counterions.This reaction was employed to effect selenium-induced ring closure reactions starting from alkenes containing internal nucleophiles.Thus, unsaturated alcohols and amides, β-diketones and β-keto esters gave the products of phenylselenoetherification.The same process occurred with dienes and unsaturated ketones when the reaction was carried out in the presence of water or methanol, respectively.Unsaturated acids, esters, and imides afforded the phenylselenolactonization products.
N-PHENYLSELENOPHTHALIMIDE (NPSP) A VALUABLE SELENENYLATING AGENT
Nicolaou, K. C.,Petasis, N. A.,Claremon, D. A.
, p. 4835 - 4842 (2007/10/02)
The phenylseleno group (PhSe) has evolved in recent years as a very useful and versatile functionality.Its facile introduction into organic molecules and its subsequent oxidative or reductive removal, has allowed many important synthetic transformations.D
ORGANOSELENIUM-INDUCED CYCLIZATIONS IN ORGANIC SYNTHESIS
Nicolaou, K.C.
, p. 4097 - 4109 (2007/10/02)
A number of organoselenium reagents are introduced as efficient initiators of ring closures leading from unsaturated substrates to lactones, cyclic ethers, cyclic thioethers, N-heterocycles and carbocycles.These cyclizations often proceed with high ring selectivity and stereoselectivity and are accompained by the incorporation of the phenylseleno group (PheSe) into the final product.Methods are described for the effective removal of this group (PheSe) by oxidation or reduction achieving unsaturation or saturation.Finally the successful application of this Se-based methodology to the synthesis of stable and biologically active prostacyclins is outlined.Representative experimental procedures are included.
Cyclofunctionalisation of unsaturated acids with benzeneselenenyl chloride. Kinetic and thermodynamic aspects of the rules for ring closure
Clive, Derrick L.J.,Russell, Charles G.,Chittattu, Gim,Singh, Alok
, p. 1399 - 1408 (2007/10/02)
Experimental procedures are described for the synthetically useful reaction by which olefinic acids are converted into lactones carrying a benzeneseleno-group. Data are presented to define some of the mechanistic details of this type of cyclofunctionalisation and kinetic and thermodynamic factors relevant to the Rules for Ring Closure are discussed. A nomenclature is introduced for a treatment of ring-fusion stereochemistry.
