Reaction of diaryl disulfides with nitroarenes

doi:10.11949/j.issn.0438-1157.20161755

CIESC Journal ›› 2017, Vol. 68 ›› Issue (6): 2394-2398.DOI: 10.11949/j.issn.0438-1157.20161755

Previous Articles Next Articles

Reaction of diaryl disulfides with nitroarenes

LI Shuyan^1,2, SUN Lina^1,2, SHEN Shujun^1,2, CHENG Tianxing³, CHENG Shuanghua³, CHEN Jiuxi³

1. Department of Food and Biology Engineering, Zhangzhou Institute of Technology, Zhangzhou 363000, Fujian, China;
2. The Applied Technical Engineering Center of Further Processing and Safety of Agriculture Products, Higher Education Institution in Fujian Province, Zhangzhou 363000, Fujian, China;
3. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, Zhejiang, China

Received:2016-12-15 Revised:2017-03-15 Online:2017-06-05 Published:2017-06-05
Contact: 10.11949/j.issn.0438-1157.20161755
Supported by:
supported by the Natural Science Foundation of Zhejiang Province (LY16B020012) and the Educational Foundation of Fujian Province (JA13388)

二芳基二硫醚与硝基芳烃的反应

李术艳^1,2, 孙莉娜^1,2, 沈淑君^1,2, 程天行³, 程双华³, 陈久喜³

1. 漳州职业技术学院食品与生物工程系, 福建漳州 363000;
2. 农产品深加工及安全福建省高校应用技术工程中心, 福建漳州 363000;
3. 温州大学化学与材料工程学院, 浙江温州 325035

通讯作者: 程天行
基金资助:
浙江省自然科学基金项目（LY16B020012）；福建省教育厅科技计划项目（JA13388）

Abstract

Abstract:

The cheap and readily available Rongalite^®/K₂CO₃ promoted the reaction of diaryl disulfides with nitroarenes in DMSO at 50 ℃, providing a convenient route to the synthesis of unsymmetrica diaryl sulfide. The structures of all products were characterized by ¹H NMR and ¹³C NMR. This protocol had some distinct advantages of mild conditions, readily available starting materials and simple work-up.

Key words: diaryl sulfide, nitroarenes, sodium formaldehyde sulfoxylate, diaryl sulfide, reaction mechanism

摘要：

以二芳基二硫醚（ArSSAr）和硝基芳烃（ArNO₂）为原料，在廉价易得的甲醛次硫酸氢钠（Rongalite^®）和碳酸钾（K₂CO₃）共同促进下，以二甲亚砜（DMSO）为溶剂，50℃下合成了一系列非对称二芳基硫醚衍生物，产物结构经¹H NMR和¹³C NMR确证。该方法具有反应条件温和、原料易得和操作简单等优点。

关键词: 二芳基二硫醚, 硝基芳烃, 甲醛次硫酸氢钠, 二芳基硫醚, 反应机理

CLC Number:

LI Shuyan, SUN Lina, SHEN Shujun, CHENG Tianxing, CHENG Shuanghua, CHEN Jiuxi. Reaction of diaryl disulfides with nitroarenes[J]. CIESC Journal, 2017, 68(6): 2394-2398.

李术艳, 孙莉娜, 沈淑君, 程天行, 程双华, 陈久喜. 二芳基二硫醚与硝基芳烃的反应[J]. 化工学报, 2017, 68(6): 2394-2398.

References 33

[1]	LIU L P, STELMACH J E, NATARAJAN S R, et al. Sar of 3,4-dihydropyrido[3, 2-d]pyrimidone p38 inhibi-tors[J]. Bioorg. Med. Chem. Lett., 2003, 13: 3979-3982.
[2]	LIU G, LINK J T, PEI Z, et al. Discovery of novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction (1): Identification of an additional binding pocket based on an anilino diaryl sulfide lead[J]. J. Med. Chem., 2000, 43: 4025-4040.
[3]	LIU G, HUTH J R, OLEJNICZAK E T, et al. Novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction (2): Mechanism of inhibition and structure-based improvement of pharmaceutical properties[J]. J. Med. Chem., 2001, 44: 1202-1210.
[4]	DE MARTINO G, EDLER M C, LA REGINA G, et al. New arylthioindoles: potent inhibitors of tubulin polymerization (2): Structure-activity relationships and molecular modeling studies[J]. J. Med. Chem., 2006, 49: 947-954.
[5]	LINDLEY J. Copper assisted nucleophilic-substitution of aryl halogen[J]. Tetrahedron, 1984, 40: 1433.
[6]	YAMAMOTO T, SEKINE Y. Condensation of thiophenols with aryl halides using metallic copper as a reactant. Intermediation of cuprous thiophenolates[J]. Can. J. Chem., 1984, 62: 1544-1547.
[7]	TERUYUKI K, TAKE-AKI M. Metal-catalyzed carbon-sulfur bond formation[J]. Chem. Rev., 2000, 100: 3205-3220.
[8]	KAO H L, LEE C F. Efficient copper-catalyzed S-vinylation of thiols with vinyl halides[J]. Org. Lett., 2011, 13: 5204-5207.
[9]	GUILARTE V, FERNÁNDEZ-RODRÍGUEZ M A, GARCÍA-GARCÍA P, et al. A practical, one-pot synthesis of highly substituted thiophenes and benzo[b]thiophenes from bromoenynes and o-alkynylbromobenzenes[J]. Org. Lett., 2011, 13: 5100-5013.
[10]	XU H J, ZHAO Y Q, FENG T, et al. Chan-Lam-type S-arylation of thiols with boronic acids at room temperature[J]. J. Org. Chem., 2012, 77: 2878-2884.
[11]	CHEN C K, CHEN Y W, LIN C H, et al. Synthesis of CuO on mesoporous silica and its applications for coupling reactions of thiols with aryl iodides[J]. Chem. Commun., 2010, 46: 282-284.
[12]	BAHEKARA S S, SARKATE A P, WADHAI V M, et al. CuI catalyzed C—S bond formation by using nitroarenes[J]. Catal. Commun., 2013, 41: 123-125.
[13]	REZAEI N, MOVASSAGH B. Polystyrene resin-supported CuI-cryptand 22 complex: a highly efficient and reusable catalyst for the formation of aryl-sulfur bonds in aqueous media[J]. Tetrahedron Lett., 2016, 57: 1625-1628.
[14]	LAI C S, KAO H L, WANG Y J, et al. A general rhodium-catalyzed cross-coupling reaction of thiols with aryl iodides[J]. Tetrahedron Lett., 2012, 53: 4365-4367.
[15]	ZHANG P F, YUAN J Y, LI H R, et al. Mesoporous nitrogen-doped carbon for copper-mediated Ullmann-type C-O/-N/-S cross-coupling reactions[J]. RSC Adv., 2013, 3: 1890-1895.
[16]	SINGH G, KUMAR A, MALIK S, et al. TBAHS catalyzed coupling reactions of aryl iodides and aryl bromides with thiols under solvent free conditions[J]. Hetero. Lett., 2013, 3: 183-190.
[17]	GUZMÁN-PERCÁSTEGUI E, HERNÁNDEZ D J, CASTILLO I. Calix
[8]	arene nanoreactor for Cu(I)-catalyzed C—S coupling[J]. Chem. Commun., 2016, 52: 3111-3114.
[18]	PANDA N, JENA A K, MOHAPATRA S. Heterogeneous magnetic catalyst for S-arylation reactions[J]. Appl. Catal. A—Gen., 2012, 433/434: 258-264.
[19]	LAN M T, WU W Y, HUANG S H, et al. Reusable and efficient CoCl2·6H2O/cationic 2,2'-bipyridyl system-catalyzed S-arylation of aryl halides with thiols in water under air[J]. RSC Adv., 2011, 1: 1751-1755.
[20]	MOVASSAGH B, TAKALLOU A, MOBARAKI A. Magnetic nanoparticle-supported Pd(Ⅱ)-cryptand 22 complex: an efficient and reusable heterogeneous precatalyst in the Suzuki-Miyaura coupling and the formation of aryl-sulfur bonds[J]. J. Mol. Catal. A: Chem., 2015, 401: 55-65.
[21]	FRINDY S, EL KADIB A, LAHCINI M, et al. Copper nanoparticles stabilized in a porous chitosan aerogel as a heterogeneous catalyst for C—S crosscoupling[J]. ChemCatChem, 2015, 7: 3307-3315.
[22]	FU W Q, LIU T T, FANG Z X, et al. High activity and stability in the cross-coupling of aryl halides with disulfides over Cu-doped hierarchically porous zeolite ZSM-5[J]. Chem. Commun.，2015, 51: 5890-5893.
[23]	ROSTAMI A, ROSTAMI A, GHADERI A. Copper-catalyzed thioetherification reactions of alkyl halides, triphenyltin chloride, and arylboronic acids with nitroarenes in the presence of sulfur sources[J]. J. Org. Chem., 2015, 80: 8694-8704.
[24]	MITSUDOME T, TAKAHASHI Y, MIZUGAKI T, et al. Hydrogenation of sulfoxides to sulfides under mild conditions using ruthenium nanoparticle catalysts[J]. Angew. Chem., Int. Ed., 2014, 53: 8348-8351.
[25]	SEBASTIAN KRACKL S, COMPANY A, ENTHALER S. Low-valent molybdenum-based dual pre-catalysts for highly efficient catalytic epoxidation of alkenes and deoxygenation of sulfoxides[J]. ChemCatChem, 2011, 3: 1186-1192.
[26]	JANG Y, KIM K T, JEON H B. Deoxygenation of sulfoxides to sulfides with thionyl chloride and triphenylphosphine: competition with the pummerer reaction[J]. J. Org. Chem., 2013, 78: 6328-6331.
[27]	ENTHALER S. A straightforward zinc-catalysed reduction of sulfoxides to sulfides, Enthaler, Stephan[J]. Catal. Sci. Technol., 2011, 1: 104-110.
[28]	ABBASI M, MOHAMMADIZADEH M R, MORADI Z. Efficient reduction of sulfoxides with NaHSO3 catalyzed by I2[J]. Tetrahedron Lett., 2015, 56: 6610-6613.
[29]	YOO B W, YU B R, YOON C M. A facile and efficient procedure for the deoxygenation of sulfoxides to sulfides with the HfCl4/Zn system[J]. J. Sulfur Chem., 2015, 36: 358-363.
[30]	AMIRI K, AMIN ROSTAMI A, SAMADI S, et al. Cu-ZSM5 as reusable catalyst for the one-pot, odorless and ligand-free C—S bond formation[J]. Catal. Comm., 2016, 86: 108-112.
[31]	CHEN J X. Rongalite[J]. Synlett, 2012, 23: 157-158.
[32]	GUO W X, LV G S, CHEN J X, et al. Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to a,b-unsaturated ketones/esters: an odorless synthesis of α,β-sulfido carbonyl compounds[J]. Tetrahedron, 2010, 66: 2297-2300.
[33]	GUO W X, CHEN J X, WU H Y, et al. Rongalite® promoted highly regioselective synthesis of β-hydroxy sulfides by ring-opening of epoxides with disulfides[J]. Tetrahedron, 2009, 65: 5240-5243.

Reaction of diaryl disulfides with nitroarenes

二芳基二硫醚与硝基芳烃的反应

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References 33

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	YE Kai, LIU Xianghua, JIANG Yue, YU Ying, ZHAO Yafei, ZHUANG Ye, ZHENG Jinbao, CHEN Binghui. Combing low-temperature plasma with CeO₂/13X for toluene degradation [J]. CIESC Journal, 2021, 72(7): 3706-3715.
[2]	ZHU Qianqian, JIN Haibo, GUO Xiaoyan, HE Guangxiang, MA Lei, ZHANG Rongyue, GU Qingyang, YANG Suohe. Study on synthesis of ε-caprolactone with MgO catalysis by Baeyer-Villiger green oxidation of cyclohexanone in H₂O₂/acetonitrile system [J]. CIESC Journal, 2021, 72(5): 2638-2646.
[3]	Gang WANG,Xuezhi DUAN,Weikang YUAN,Xinggui ZHOU. Mechanistic insights into catalytic isomerization of propylene oxide over TS-1 [J]. CIESC Journal, 2021, 72(10): 5150-5158.
[4]	Hong ZHANG, Liu TANG. Study on reaction mechanism of p-type dopant Cp₂Mg in MOCVD gas phase [J]. CIESC Journal, 2020, 71(7): 3000-3008.
[5]	Yan JIN, Qian YANG, Wenbin ZHAO, Baoshan HU. Catalytic reaction system for controllable synthesis of graphene with chemical vapor deposition [J]. CIESC Journal, 2020, 71(6): 2564-2585.
[6]	Lufeng WANG, Xin QIAN, Lifang DENG, Haoran YUAN. Recent progress on catalysts about electrochemical synthesis of ammonia from nitrogen [J]. CIESC Journal, 2019, 70(8): 2854-2863.
[7]	Yonggang CHENG, Jiao LIU, Zhennan HAN, Lei SHI, Guangwen XU. Transfer dynamics and reaction control mechanism over methanation catalyst particles in transport bed [J]. CIESC Journal, 2019, 70(8): 2876-2887.
[8]	Tianshui LIANG, Zongying WANG, Kun GAO, Runwan LI, Zheng WANG, Wei ZHONG, Jun ZHAO. Analysis of fire suppression effectiveness of ultra-fine water mist containing iron compounds additives in cup burner [J]. CIESC Journal, 2019, 70(3): 1236-1242.
[9]	ZHANG Yi, LI Jianbo, WANG Quanhai, LU Xiaofeng. Simulation of NO_x formation in novel dual circulating fluidized-bed boiler [J]. CIESC Journal, 2018, 69(4): 1703-1713.
[10]	ZHANG Hongmei, LIN Feng, REN Mingqi, LI Jinlian, HAO Yulan, WU Hongjun, ZHAO Jingying, ZHAO Liang, HE Yongdian. Free radical models of small molecular alkane pyrolysis [J]. CIESC Journal, 2017, 68(4): 1423-1433.
[11]	ZHANG Guangjie, GENG Yanlou, AN Hualiang, ZHAO Xinqiang, WANG Yanji. Synthesis of propylene carbonate from CO₂ and 1,2-propylene glycol on fixed-bed reactor and its reaction mechanism catalyzed by Zn(OAc)₂/AC [J]. CIESC Journal, 2015, 66(2): 567-575.
[12]	WANG Caijun, LU Shaojie, WANG Ping. Sub-grid scale combustion model based on REDIM method and its application [J]. CIESC Journal, 2015, 66(12): 4948-4959.
[13]	WANG Rongjie, SHEN Benxian, MA Jian, ZHAO Jigang. Ring-open reaction mechanism of sulfur S₈ based on density functional theory [J]. CIESC Journal, 2015, 66(10): 3919-3924.
[14]	WANG Yao, DI Zuoxing, LI Yuxin, WANG Dezheng, WEI Fei. Multiphase catalytic reactors for methanol-to-olefins [J]. CIESC Journal, 2014, 65(7): 2474-2484.
[15]	ZHANG Juntao，LIU Jiankang，LIANG Shengrong，ZHONG Hanbin. Recent developments in catalyst for waste plastic to fuels via chemical conversion process [J]. Chemical Industry and Engineering Progree, 2014, 33(10): 2644-2649.