Oxidation of Diphenyl Diselenide with 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate):A Method for the Electrophilic Phenylselenenylation of Alkenes

doi:10.11944/j.issn.1000-0518.2016.10.160108

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (10): 1218-1220.DOI: 10.11944/j.issn.1000-0518.2016.10.160108

• Communications • Previous Articles

Oxidation of Diphenyl Diselenide with 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate):A Method for the Electrophilic Phenylselenenylation of Alkenes

TIAN Zaiwen,LIU Ze,YU Pei,ZHANG Wanxuan()

Hubei Collaborative Innovation Center for Advanced Organic Chemical Material,Key Laboratory for the Synthesis and Application of Organic Functional Molecules,Ministry of Education,Hubei University,Wuhan 430062,China

Received:2016-03-14 Accepted:2016-06-15 Published:2016-10-08 Online:2016-10-08
Contact: ZHANG Wanxuan
Supported by:
Supported by the Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei University, China(No.2013-KL-009)

Abstract

Abstract:

Diphenyl diselenide was oxidized by Selectfluor and added to alkenes catalyed by silver triflate. The reaction performed in CH₂Cl₂ in the presence of water or alcohol leading to β-hydroxy or β-alkoxy selenides in good yields in the range of 72%~94%. The reaction conditions and the scope of substrates were discussed. This method has some advantages such as mild reaction conditions and high yields.

Key words: Selectfluor, alkene, diphenyl diselenide, oxidation, addition

TIAN Zaiwen, LIU Ze, YU Pei, ZHANG Wanxuan. Oxidation of Diphenyl Diselenide with 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate):A Method for the Electrophilic Phenylselenenylation of Alkenes[J]. Chinese Journal of Applied Chemistry, 2016, 33(10): 1218-1220.

References

[1]	Wirth T.Introduction and General Aspects[M]. Organoselenium Chemistry. Springer Berlin Heidelberg,2000:1-5.
[2]	Dias G R M,de Almeida T M,Sudati J H,et al. Diphenyl Diselenide Supplemented Diet Reduces Depressive-like Behavior in Hypothyroid Female Rats[J]. Physiol Behav,2014,124(30):116-122,and references therein.
[3]	Mariappan K,Alaparthi M,Hoffman M,et al. Improved Selectivity for Pb(ii) by Sulfur, Selenium and Tellurium Analogues of 1,8-Anthraquinone-18-crown-5:Synthesis, Spectroscopy, X-ray Crystallography and Computational Studies[J]. Dalton Trans,2015,44(26):11774-11787,and references therein.
[4]	Tiecco M,Testaferri L,Tingoli M,et al.The Reaction of Diphenyl Diselenide with Peroxydisulphate Ions in Methanol a Convenient Procedure to Effect the Methoxyselenenylation of Alkenes[J]. Tetrahedron Lett,1989,30(11):1417-1420.
[5]	Tingoli M,Tiecco M,Testaferri L,et al.Iodosobenzene Diacetate and Diphenyl Diselenide:An Electrophilic Selenenylating Agent of Double Bonds[J]. Synth commun,1998,28(10):1769-1778.
[6]	Lee D H,Kim Y H.Regioselective Phenylselenenylation at the 5-Position of Pyrimidine Nucleosides Mediated by Manganese(Ⅲ) Acetate[J]. Synlett,1995,(4):349-350.
[7]	Santoro S,Santi C,Sabatini M,et al.Eco-friendly Olefin Dihydroxylation Catalyzed by Diphenyl Diselenide[J]. Adv Synth Catal,2008,350(18): 2881-2884.
[8]	Tiecco M,Testaferri L,Temperini A,et al.Oxidation of Diphenyl Diselenide with 2,3-Dichloro-5,6-dicyanobenzoquinone(DDQ). A New Method for the Electrophilic Phenylselenenylation of Alkenes under Mild Conditions[J]. Synlett,2001,(11):1767-1771.
[9]	Gruttadauria M,Meo P L,Riela S,et al.Lipase-catalyzed Resolution of β-Hydroxy Selenides[J]. Tetrahedron: Asym,2006,17(18):2713-2721.
[10]	Vieira A A,Azeredo J B,Godoi M,et al.Catalytic Chalcogenylation under Greener Conditions:A Solvent-free Sulfur- and Seleno-Functionalization of Olefins via I2/DMSO Oxidant System[J]. J Org Chem,2015,80(4):2120-2127.
[11]	Zhang C,Li Z,Zhu L,et al.Silver-catalyzed Radical Phosphonofluorination of Unactivated Alkenes[J]. J Am Chem Soc,2013,135(38):14082-14085.

[1]	Yu-Wen YANG, Jing-Yao QI, Lin LI, Guo-Ning CHU, Sai WANG, Yu ZHANG, Shuang ZHANG. Selective Oxidation of 5-Hydroxymethylfurfural to 2，5-Furandicarboxylic Acid over Ru Supported on Magnetic NiFe₂O₄ [J]. Chinese Journal of Applied Chemistry, 2023, 40(6): 879-887.
[2]	Feng ZHU, Xiao-Lian PENG, Wen-Bin ZHANG. Research Progress in the Effects of Proton Acceptor/Donor on Electrocatalytic Reactions [J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 666-680.
[3]	Hua-Yu WANG, Chao ZHANG, Ke-Ming CHEN, Ming GE. Research Progress of Metal-organic Framework MIL-88A（Fe） and Its Composites in Water Treatment [J]. Chinese Journal of Applied Chemistry, 2023, 40(2): 155-168.
[4]	Jun-Jie ZHANG, Yun-Jiao SHEN, Li-Ying MA, Peng-Hui WANG, Lei WANG, Yu-Lin DAI, Lei ZHAO. Study on Extract Composition of American Ginseng Flower in Oxidative-Induced H9c2 Cardromyocytes by LC-MS [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 126-133.
[5]	Yan-Qin CHENG, Zhuo-Xi LI, You-Di WANG, Juan-Juan XU, Zheng BIAN. Structurally Simplified 4-Hydroxyprolinamide for Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroolefins [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 146-154.
[6]	Dan ZHANG, Run-Mei SHANG, Zhen-Tao ZHAO, Jun-Hua LI, Jin-Juan XING. Selective Oxidation of Methanol to Dimethoxymethane over V/Ce⁃Al₂O₃ Catalysts [J]. Chinese Journal of Applied Chemistry, 2022, 39(9): 1429-1436.
[7]	Bing WANG, Min TANG, Ying WANG, Zhi-Guang LIU. Preparation of Y₂O₃⁃Dopped SiC Ceramics by Micro⁃oxidation Sintering and Removal of Cd²⁺ in Mimic Wastewater [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1312-1318.
[8]	You-San ZHOU, Yi-Cheng ZHANG, Si-Yu WU, Fei ZHA, De-Jun CHEN, Yue CHANG. Catalytic Performance of Cu‑Doped Calcium Aluminum Layered Double Hydrotalcites for the Oxidation of Cumene to Cumene Hydrogen Peroxide [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 941-948.
[9]	Ke WANG, Xiao WANG, Shu-Yan SONG. Recent Advances in Direct Oxidation of Methane to Methanol [J]. Chinese Journal of Applied Chemistry, 2022, 39(4): 540-558.
[10]	Li-Zhi SUN, Hao LYU, Xiao-Wen MIN, Ben LIU. Mesoporous Palladium⁃Boron Alloy Nanocatalysts： Synthesis and Performance in Methanol Oxidation Electrocatalysis [J]. Chinese Journal of Applied Chemistry, 2022, 39(4): 673-684.
[11]	Chen-Chen ZHANG, Yu-Han LIU, Wen-Jie ZHAO, Bai-Jun LIU, Zhao-Yan SUN, Wan-Li LIU, Yan-Miao WANG, Wei HU. Preparation of Oxidized Organosolv Lignin⁃based Hydrophilic Sizing Agent and Its Application in Polypropylene [J]. Chinese Journal of Applied Chemistry, 2022, 39(12): 1854-1861.
[12]	Ying CHEN, Tian-Ding HU, Yun-Li LIU, Pu ZHANG, Yun-Fei ZHI, Shao-Yun SHAN. Research Progress on Chemical Resourse Utilization of Sulfur Dioxide [J]. Chinese Journal of Applied Chemistry, 2022, 39(02): 223-234.
[13]	TIAN Shu-Yang, LYU Rong-Wen. Solvent-Free Oxidation of Benzyl Alcohol to Benzaldehyde Catalyzed by Magnesium Oxide Supported Bimetallic Gold-Palladium [J]. Chinese Journal of Applied Chemistry, 2021, 38(7): 789-799.
[14]	ZHANG Xi-Yue, SUN Hong-Juan, PENG Tong-Jiang, WANG Ya. Preparation and Characterization of Graphite Oxide with High Cation Exchange Capacity by a Potassium Persulfate Intercalation Expansion-Oxidation Method [J]. Chinese Journal of Applied Chemistry, 2021, 38(7): 816-824.
[15]	LUO Ce, YAN Yan, LI Jian, LIU Ting, BAI Huan-Huan, LU Fan, FENG Jing. Determination of Trace Iron in High Purity Titanium by Methane Dynamic Reaction-Inductively Coupled Plasma Mass Spectrometry Standard Addition Method [J]. Chinese Journal of Applied Chemistry, 2021, 38(7): 874-880.

Oxidation of Diphenyl Diselenide with 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate):A Method for the Electrophilic Phenylselenenylation of Alkenes

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments