- Time-economical synthesis of selenofunctionalized heterocycles via I2O5-mediated selenylative heterocyclization
-
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
- 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)
-
- (o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors
-
(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, decharcogenative, and decarboxylative borylations proceeded in the presence of a radica
- Suzuki, Kensuke,Nishimoto, Yoshihiro,Yasuda, Makoto
-
supporting information
p. 3968 - 3973
(2020/12/30)
-
- Preparation of selenofunctionalized heterocycles via iodosobenzene-mediated intramolecular selenocyclizations of olefins with diselenides
-
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.
- Wang, Peng-Fei,Yi, Wei,Ling, Yong,Ming, Liang,Liu, Gong-Qing,Zhao, Yu
-
supporting information
p. 2587 - 2591
(2021/03/15)
-
- Electrochemical Difunctionalization of Olefines: Access to Selenomethyl-Substituted Cyclic Ethers or Lactones
-
A metal- and oxidant-free electrochemical method for preparing selenomethyl-substituted cyclic ethers or lactones via difunctionalization of olefines is presented. A series of selenomethyl-substituted cyclic ethers, particularly 9- and 11- membered, selen
- Meng, Xiu-Jin,Zhong, Ping-Fu,Wang, Yu-Mei,Wang, Heng-Shan,Tang, Hai-Tao,Pan, Ying-Ming
-
supporting information
p. 506 - 511
(2019/12/24)
-
- Automated Electrochemical Selenenylations
-
Integrated electrochemical reactors in automated flow systems were utilised for selenenylation reactions. The automation allowed multiple electrochemical reactions of a programmed sequence to be performed in a fully autonomous way. Many functionalised selenenylated products were synthesised in short reaction times in good to high yields.
- Amri, Nasser,Wirth, Thomas
-
supporting information
p. 1751 - 1761
(2020/06/08)
-
- Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides
-
The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group
- Zhang, Qing-Bao,Yuan, Pan-Feng,Kai, Liang-Lin,Liu, Kai,Ban, Yong-Liang,Wang, Xue-Yang,Wu, Li-Zhu,Liu, Qiang
-
supporting information
p. 885 - 889
(2019/02/14)
-
- A mild and efficient procedure for alkenols oxyselenocyclization by using ionic liquids
-
A mild and efficient procedure for the oxyselenocyclization of unsaturated alcohols by treatment with phenylselenyl chloride using ionic liquids as solvents/catalyzers has been developed. The reaction proceeds instantaneously under mild conditions with ab
- Kosti?, Marina,Verdía, Pedro,Fernández-Stefanuto, Verónica,Puchta, Ralph,Tojo, Emilia
-
supporting information
(2019/01/08)
-
- Synthesis, crystal and solution structures and antimicrobial screening of palladium(II) complexes with 2-(phenylselanylmethyl)oxolane and 2-(phenylselanylmethyl)oxane as ligands
-
Two novel Pd(II) complexes with 2-(phenylselanylmethyl)oxolane and 2-(phenylselanylmethyl)oxane as ligands were synthesized. The crystal and molecular structure of the complexes has been determined by single crystal X-ray diffraction. It turned out for bo
- Bugari, Zorica M.,Divac, Vera M.,Kosti, Marina D.,Jankovi, Nenad .,Heinemann, Frank W.,Radulovi, Niko S.,Stojanovi-Radi, Zorica Z.
-
-
- Synthesis, crystal and solution structures and antimicrobial screening of palladium(II) complexes with 2-(phenylselanylmethyl)oxolane and 2-(phenylselanylmethyl)oxane as ligands
-
Two novel Pd(II) complexes with 2-(phenylselanylmethyl)oxolane and 2-(phenylselanylmethyl)oxane as ligands were synthesized. The crystal and molecular structure of the complexes has been determined by single crystal X-ray diffraction. It turned out for bo
- Bugar?i?, Zorica M.,Divac, Vera M.,Kosti?, Marina D.,Jankovi?, Nenad ?.,Heinemann, Frank W.,Radulovi?, Niko S.,Stojanovi?-Radi?, Zorica Z.
-
-
- Visible-light-promoted selenofunctionalization of alkenes
-
A visible-light-promoted method for the selenofunctionalization (and tellurofunctionalization) of alkenes has been developed. This method obviates the prepreparation of moisture-sensitive chalcogen electrophiles. The experimental setup is simple, and supe
- Conner, Elizabeth S.,Crocker, Katherine E.,Fernando, Ranelka G.,Fronczek, Frank R.,Stanley, George G.,Ragains, Justin R.
-
supporting information
p. 5558 - 5561
(2013/11/19)
-
- An efficient route to phenylselenoethers in the presence of Ag2O
-
An efficient protocol for the preparation of phenylselenoethers from unsaturated alcohols using phenylselenenyl halides at room temperature was developed. The procedure employs phenylselenenyl chloride and bromide, some Δ 4- and Δ 5-
- Bugarcic, Zorica M.,Divac, Vera M.,Gavrilovic, Mariana P.
-
p. 985 - 988
(2008/03/17)
-
- An Improved Procedure for Phenylselenoetherification of Some Δ5-Alkenols Using Pyridine, Ag2o, and Some Lewis Acids as Catalysts
-
An improved procedure for intramolecular cyclization of some Δ5-alkenols, using PhSeX (X = Cl, Br) has been developed. We found that cyclization can be facilitated in the presence of pyridine, Ag 2O, and some Lewis acids as catalysts
- Bugar?i?, Zorica M.,Mojsilovi?, Biljana M.
-
p. 146 - 149
(2007/10/03)
-
- Phenylselenoetherification of Some Δ5-Alkenols in the Presence of Pyridine, Ag2O, and AgOAc as Additives
-
An improved procedure for intramolecular cyclization of some Δ 5-aikenols using PhSeX (X=Cl, Br) was developed. We found that cyclization can be facilitated in the presence of pyridine, Ag2O, and AgQAc as additives. Thus, a catalytic
- Bugar?i?, Zorica M.,Gavrilovi?, Marijana
-
p. 1359 - 1363
(2007/10/03)
-
- Oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). A new method for the electrophilic phenylselenenylation of alkenes under mild conditions
-
The oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) represents a convenient mild method to produce a strongly electrophilic phenylselenium reagent. Clean phenylseleno methoxylations and hydroxylations of alkenes containing different types of functional groups can be effected by working in methanol or in acetonitrile and water, respectively. This new electrophilic reagent can also be employed to promote efficient cyclization reactions of alkenols to tetrahydrofurans or of alkenoic acids to lactones.
- Tiecco,Testaferri,Temperini,Bagnoli,Marini,Santi
-
p. 1767 - 1771
(2007/10/03)
-
- Studies of the reactions of some benzenalkenyl ethers with benzenselenenyl halides
-
Intramolecular cyclization of some benzenalkenyl ethers with benzenselenenyl halides (PhSeX, X=Cl and Br) at different temperatures (- 78°C, 0°C and room temperature) has been investigated. It has been found that Δ4-alkenyl benzyl ethers. affor
- Bugar?i?, Zorica,Konstantinovi?, Stanimir,Mojsilovi?, Biljana
-
p. 728 - 731
(2007/10/03)
-
- Iodosobenzene diacetate and diphenyl diselenide: An electrophilic selenenylating agent of double bonds
-
Phenylseleno-acetoxylation, hydroxylation, etherification and lactonization products are obtained in good yields from the reaction of alkenes with diphenyl diselenide and iodosobenzene diacetate, in acetonitrile.
- Tingoli, Marco,Tiecco, Marcello,Testaferri, Lorenzo,Temperini, Andrea
-
p. 1769 - 1778
(2007/10/03)
-
- Superelectrophilic selenium. A new simple method for generation of areneselenenyl trifluoroacetates and triflates
-
Areneselenenyl trifluoroacetates and triflates were obtained by comproportionation of an areneseleninic anhydride with the corresponding diselenide in the presence of trifluoroacetic or triflic anhydride. This represents an attractive alternative to the previously reported1-5 route for preparation of these reagents.
- Kutateladze, Andrei G.,Kice, John L.,Kutateladze, Tatiana G.,Zefirov, Nikolai S.,Zyk, Nikolai V.
-
p. 1949 - 1952
(2007/10/02)
-
- Regioselectivity in Cyclofunctionalization of Olefinic Alcohols with Benzeneselenenyl Halides at Different Temperatures
-
The regioselectivity in cyclofunctionalization of some acyclic olefinic alcohols with benzeneselenenyl halides (PhSeCl and PhSeBr) at different temperatures (-78 deg C, 0 deg C and room temperature) is investigated.It has been found that Δ4- and Δ5-alkenols are converted into five- and/or six-membered cyclic phenyl selenoethers, the yield of which decreases with increasing temperature.PhSeCl has been found to be more efficient than PhSeBr in the cyclization reactions. Key Words: Olefinic alcohols / Cyclofunctionalization / Benzeneselenenyl halides
- Konstantinovic, Stanimir,Bugarcic, Zorica,Milosavljevic, Slobodan,Schroth, Gerhard,Mihailovic, Mihailo Lj.
-
p. 261 - 268
(2007/10/02)
-
- Formation and Electrophilic Reactions of Benzeneselenenyl p-Toluenesulfonate. Perparation and Properties of Addition Products with Acetylenes
-
Benzeneselenenyl p-toluenesulfonate (1) was generated in situ by the reaction of silver p-toluenesulfonate with benzeneselenenyl chloride in acetonitrile.The reagent reacted with acetylenes by electrophilic 1,2-addition to afford the β-(phenylseleno)vinyl p-toluenesulfonates 2-12, generally in high yield.The latter were formed preferentially by anti addition, but with poor regioselectivity, unless a strongly orienting group (e.g., phenyl) was present.Selenenyl sulfonate 1 was also unexpectedly produced via radical pathways by heating p-toluenesulfonic acid with AIBN in the presence of diphenyl diselenide, or from the pyrolysis of sulfinyl sulfone 15 with the diselenide.The regioisomeric adducts 3 and 4 were prepared from 1 and 1-decyne, and both underwent elimination with potassium tert-butoxide to afford the acetylenic selenide 19 initially, which isomerized to a 6:1 mixture of the propargylic and allenic selenides 20 and 21 upon further equilibration.A Fritsch-Buttenberg-Wiechell rearrangement is proposed for the elimination of 4.The syn elimination of the selenoxide of 4 required forcing conditions and afforded only ca. 20percent of the corresponding allenic sulfonate 22.The electrophile 1 induced the efficient cyclization of 5-hexen-1-ol and 4-pentenoic acid to the corresponding pyran 24 and lactone 25, respectively.It failed to cyclize alkynols, but afforded the lactones 28 and 29 from 4-pentynoic acid in low yield.
- Back, Thomas G.,Muralidharan, K. Raman
-
p. 2781 - 2787
(2007/10/02)
-
- Oxidative Cleavage of Diselenide by m-Nitrobenzenesulfonyl Peroxide. Novel Method for the Electrophilic Benzeneselenenylations of Olefins and Aromatic Rings
-
Diphenyl diselenide was found to be readily converted into benzeneselenenyl-m-nitrobenzenesulfonate (PhSeOSO2C6H4NO2-m) by treating with m-nitrobenzenesulfonyl peroxide.When the selenenyl sulfonate thus formed was allowed to react in situ with olefins, such as cyclohexene, 1-octene, or styrene, in the presence of various nucleophiles, the adducts of benzeneselenenyl group and a nucleophile were obtained.As the nucleophiles water, methanol, acetic acid, phenol, and anisole could be employed; oxyselenenylated : R=H, Me, Ac, and Ph) and arylselenenylated : R=H and Me) adducts were afforded.Phenol gave oxyselenenylated products in cyclohexene or 1-octene and arylselenenylated products in styrene.Efficient intramolecular cyclizations of unsaturated alcohols and carboxylic acids were similarly performed by the selenenyl sulfonate to afford corresponding benzeneselenenylated cyclic ethers and lactones.The selenenyl sulfonate was also found to be a highly reactive benzeneselenenylating reagent for aromatic rings, such as anisole, phenol, acetanilide, toluene, and benzene.
- Yoshida, Masato,Sasage, Shuichi,Kawamura, Kyoko,Suzuki, Takashi,Kamigata, Nobumasa
-
p. 416 - 422
(2007/10/02)
-
- Electrochemical cyclization of unsaturated hydroxy compounds. Phenylselenoetherification and phenylselenolactonization
-
Phenylselenoetherification and phenylselenolactonization were performed in one step by electrolysis of unsaturated alcohols or carboxylic acids and diphenyl diselenide in organic solvent containing halide ions as mediators.
- Vukicevic,Konstantinovic,Mihailovic
-
p. 859 - 865
(2007/10/02)
-
- Ring-Closure Reactions Initiated by the Peroxydisulfate Ion Oxidation of Diphenyl Diselenide
-
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.
- Tiecco, M.,Testaferri, L.,Tingoli, M.,Bartoli, D.,Balducci, R.
-
p. 429 - 434
(2007/10/02)
-
- Formation of Electrophilic Selenium Species (PhSe+) by Photo-oxidative (Single-electron Transfer) Cleavage of Diphenyl Diselenide
-
Photosensitized (single-electron transfer) cleavage of diphenyl diselenide to give electrophilic selenium species (PhSe+) is reported.
- Pandey, G.,Rao, V. Jayathirtha,Bhalerao, U. T.
-
p. 416 - 417
(2007/10/02)
-
- CYCLIZATION OF OLEFINIC ALCOHOL BY BENZENESELENENYL TRIFLATE
-
Cyclization of 4-, 5-, and 6-hydroxyalkenes with benzeneselenenyl triflate afforded corresponding tetrahydrofurans and -pyrans.
- Murata, Shizuaki,Suzuki, Toshiyasu
-
p. 4297 - 4298
(2007/10/02)
-
- ELECTROCHEMICAL CYCLIZATION OF UNSATURATED HYDROXY COMPOUNDS. PART I. PHENYLSELENOETHERIFICATION
-
One-step cyclization of alkenols has been accomplished by electrooxidative phenylselenoetherification.The reaction was performed by electrolysis of unsaturated alcohols and diphenyl diselenide in methylene chloride containing tetraethylammonium bromide.
- Mihailovic, M. Lj.,Konstantinovic, S.,Vukicevic, R.
-
p. 4343 - 4346
(2007/10/02)
-
- ORGANOSELENIUM-INDUCED CYCLIZATIONS IN ORGANIC SYNTHESIS
-
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.
- Nicolaou, K.C.
-
p. 4097 - 4109
(2007/10/02)
-
- Phenylselenoetherification. A Highly Efficient Cyclization Process for the Synthesis of O- and S-Heterocycles
-
Phenylselenoetherification, a new cyclization procedure based on organoselenium chemistry, is described in detail.Unsaturated hydroxy and thio compounds were subjected to this new cyclization process to afford a series of phenyl selenoethers and phenyl selenothioethers which were transformed to a variety of heterocyclic systems by reductive or oxidative removal of the selenium group.Applications to the synthesis of muscarine analogues are described.
- Nicolaou, K. C.,Magolda, R. L.,Sipio, W. J.,Barnette, W. E.,Lysenko, Z.,Joullie, M. M.
-
p. 3784 - 3793
(2007/10/02)
-