Research Progress on Dehalogenation Reaction

doi:10.6023/cjoc201306023

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (11): 2291-2297.DOI: 10.6023/cjoc201306023 Previous Articles Next Articles

Reviews

脱卤反应研究进展

薛福玲^a, 熊金锋^a, 莫广珍^a, 彭湃^a, 陈任宏^b, 汪朝阳^a

a 华南师范大学化学与环境学院教育部环境理论化学重点实验室广州 510006;
b 广东食品药品职业学院广州 510520

收稿日期:2013-06-16 修回日期:2013-07-08 发布日期:2013-07-11
通讯作者: 汪朝阳 E-mail:wangzy@scnu.edu.cn
基金资助:
国家自然科学基金（No. 20772035）、广东省高等学校人才引进专项资金（No. 粤财教[2011]431号）、广东省自然科学基金（No. S2011010001556）资助项目.

Research Progress on Dehalogenation Reaction

Xue Fuling^a, Xiong Jinfeng^a, Mo Guangzhen^a, Peng Pai^a, Chen Renhong^b, Wang Zhaoyang^a

a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006;
b Guangdong Food and Drug Vocational College, Guangzhou 510520

Received:2013-06-16 Revised:2013-07-08 Published:2013-07-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20772035), the 3rd Talents Special Funds of Guangdong Higher Education (No. Guangdong-Finance-Education [2011]431) and the Natural Science Foundation of Guangdong Province (Nos. 5300082, S2011010001556).

Dehalogenation reaction has important applications in many fields, such as environmental protection, biochemistry and organic synthesis. Especially, more and more attention has been paid to the formation of C—H bond via the dehalogenation reaction in organic synthesis. Based on different reaction substrates, the recent research progresses on the dehalogenation reaction of C_sp³-X and C_sp²-X substrates, especially the aryl halides (including halogenated aromatic heterocycles), halogen ketones, halogenated lactones, are reviewed. It is pointed that to improve the selectivity and practicality of dehalogenation reactions is the key for their further extensive uses in organic synthesis. At the same time, the dehalogenation via photochemical reaction as a novel green chemistry route is also worthy of further study in the future.

Key words: dehalogenation reaction, palladium-catalyzed, reduction reaction, hydrogen source, photochemical reaction

Cite this article

Xue Fuling, Xiong Jinfeng, Mo Guangzhen, Peng Pai, Chen Renhong, Wang Zhaoyang. Research Progress on Dehalogenation Reaction[J]. Chin. J. Org. Chem., 2013, 33(11): 2291-2297.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Bhaskar,T.; Matsui,T.; Kaneko,J.; Uddin,M.A.; Muto,A.; Sakata,Y.Green Chem.2002,4,372.
[2] van Pee,K.-H.Angew.Chem.,Int.Ed.2003,42,3718.
[3] Li,X.-F.; Sevilla,M.D.; Sanche,L.J.Am.Chem.Soc.2003,125,8916.
[4] Osborne,R.L.; Coggins,M.K.; Terner,J.; Dawson,J.H.J.Am.Chem.Soc.2007,129,14838.[5] Lin,M.-H.; Tsai,W.S.; Lin,L.-Z.; Hung,S.-F.; Chuang,T.-H.; Su,Y.-J.J.Org.Chem.2011,76,8518.
[6] Risse,J.; Fernandez-Zumel,M.A.; Cudre,Y.; Severin,K.Org.Lett.2012,14,3060.
[7] Yang,D.-Q.; Wang,Z.-Y.; Long,Y.-H.Advanced Organic Chemistry——Structure,Reaction and Mechanism,Chemical Industry Press,Beijing,2012,p.206 (in Chinese).(杨定乔,汪朝阳,龙玉华,高等有机化学——结构、反应与机理,化学工业出版社,北京,2012,p.206.)
[8] Wang,Y.-C.; Yan,T.-H.Chem.Commun.2000,545.
[9] Buelow,M.T.; Gellman,A.J.J.Am.Chem.Soc.2001,123,1440.
[10] Huang,Z.-Z.; Tang,Y.J.Org.Chem.2002,67,5320.
[11] Wirtz,M.; Klucik,J.; Rivera,M.J.Am.Chem.Soc.2000,122,1047.
[12] Xue,F.-L.; Li,J.-X.; Mo,Y.-Q.; Wang,Z.-Y.; Chen,Q.-H.Chin.J.Org.Chem.2012,32,284 (in Chinese).(薛福玲,李建晓,莫阳青,汪朝阳,陈庆华,有机化学,2012,32,284.)
[13] Fukuzumi,S.; Mochizuki,S.; Tanaka,T.J.Phys.Chem.1990,94,722.
[14] Maji,T.; Karmakar,A.; Reiser,O.J.Org.Chem.2011,76,736.
[15] Neumann,M.; Fuldner,S.; Konig,B.; Zeitler,K.Angew.Chem.,Int.Ed.2011,50,951.
[16] Neumann,M.; Zeitler,K.Org.Lett.2012,14,2658.
[17] Narayanam,J.M.R.; Tucker,J.W.; Stephenson,C.R.J.J.Am.Chem.Soc.2009,131,8756.
[18] Li,X.-C.; Ma,J.; Liu,G.-F.; Fang,J.-Y.; Yue,S.-Y.; Guan,Y.-H.; Chen,L.-W.; Liu,X.-W.Environ.Sci.Technol.2012,46,7342.
[19] Aitken,R.A.; Hodgson,P.K.G.; Oyewale,A.O.; Morrison,J.J.Chem.Commun.1997,1163.
[20] Ji,H.-B.; Long,Q.-P.; He,Y.-B.; Yao,X.-D.Sci.China Chem.2010,53,1520.
[21] Yoneda,T.; Takido,T.; Konuma,K.J.Mol.Catal.A: Chem.2007,265,80.
[22] Gopinath,R.; Lingaiah,N.; Babu,N.S.; Suryanarayana,I.; Sai Prasad,P.S.; Obuchi,A.J.Mol.Catal.A: Chem.2004,223,289.
[23] Chen,C.-Y.; Huang,Y.-Y.; Su,W.-N.; Kaneko,K.; Kimura,M.; Takayama,H.; Wong,F.F.J.Heterocycl.Chem.2012,49,183.
[24] Kawabata,T.; Atake,I.; Ohishi,Y.; Shishido,T.; Tian,Y.; Takaki,K.; Takehira,K.Appl.Catal.B: Environ.2006,66,151.
[25] Chen,X.-B.; Hua,Q.-P.; Yuan,Q.-J.; Ding,W.; Ren,J.-M.; Zeng,B.-B.Tetrahedron Lett.2012,53,3798.
[26] Hara,T.; Mori,K.; Oshiba,M.; Mizugaki,T.; Ebitani,K.; Kaneda,K.Green Chem.2004,6,507.
[27] Hara,T.; Kaneta,T.; Mori,K.; Mitsudome,T.; Mizugaki,T.; Ebitani,K.; Kaneda,K.Green Chem.2007,9,1246.
[28] Chang,F.; Kim,H.; Lee,B.; Park,H.G.; Park,J.Bull.Korean Chem.Soc.2011,32,1074.
[29] Moon,J.; Lee,S.J.Organomet.Chem.2009,694,473.
[30] Chen,J.-B.; Zhang,Y.-S.; Yang,L.-Q.; Zhang,X.; Liu,J.-P.; Li,L.; Zhang,H.-B.Tetrahedron 2007,63,4266.
[31] Navarro,O.; Marion,N.; Oonishi,Y.; Kelly,R.A.; Nolan,S.P.J.Org.Chem.2006,71,685.
[32] Navarro,O.; Kaur,H.; Mahjoor,P.; Nolan,S.P.J.Org.Chem.2004,69,3173.
[33] Nakao,R.; Rhee,H.; Uozumi,Y.Org.Lett.2005,7,163.
[34] Abazari,R.; Heshmatpour,F.; Balalaie,S.ACS Catal.2013,3,139.
[35] Shiraishi,Y.; Takeda,Y.; Sugano,Y.; Ichikawa,S.; Tanaka,S.; Hirai,T.Chem.Commun.2011,47,7863.
[36] Zawisza,A.M.; Muzart,J.Tetrahedron Lett.2007,48,6738.
[37] Zhang,C.; Li,X.-Y.; Sun,H.-J.Inorg.Chim.Acta 2011,365,133.
[38] Stepnicka,P.; Semler,M.; Demel,J.; Zukal,A.; Cejka,J.J.Mol.Catal.A: Chem.2011,341,97.
[39] Wang,X.-J.; Zhang,L.; Lee,H.; Haddad,N.; Krishnamurthy,D.; Senanayake,C.H.Org.Lett.2009,11,5026.
[40] Chelucci,G.; Baldino,S.; Ruiu,A.J.Org.Chem.2012,77,9921.
[41] Chelucci,G.Tetrahedron Lett.2010,51,1562.
[42] Iranpoor,N.; Firouzabadi,H.; Azadi,R.J.Organomet.Chem.2010,695,887.
[43] Czaplik,W.M.; Grupe,S.; Mayer,M.; Jacobi von Wangelin,A.Chem.Commun.2010,46,6350.
[44] Weidauer,M.; Irran,E.; Someya,C.I.; Haberberger,M.; Enthaler,S.J.Organomet.Chem.2013,729,53.
[45] Breitenfeld,J.; Scopelliti,R.; Hu,X.-L.Organometallics 2012,31,2128.
[46] Patra,A.K.; Dutta,A.; Bhaumik,A.ACS Appl.Mater.Interfaces 2012,4,5022.
[47] Liang,L.; Wang,W.; Xu,F.-R.; Niu,Y.; Sun,Q.; Xu,P.Org.Lett.2013,15,2770.
[48] Mochizuki,K.; Suzuki,M.Inorg.Chem.Commun.2011,14,902.
[49] Mulder,P.; Arends,I.W.C.E.; Santoro,D.; Korth,H.-G.J.Org.Chem.2003,68,4247.
[50] Luda,M.P.; Balabanovich,A.I.J.Anal.Appl.Pyrolysis 2011,90,63.
[51] Liang,X.-M.; Devine,C.E.; Nelson,J.; Sherwood Lollar,B.; Zinder,S.; Edwards,E.A.Environ.Sci.Technol.2013,47,2378.
[52] Manna,D.; Mugesh,G.J.Am.Chem.Soc.2012,134,4269.
[53] Hayashi,Y.; Shoji,M.; Kishida,S.Tetrahedron Lett.2005,46,681.
[54] Harmata,M.; Zheng,P.-G.; Schreiner,P.R.; Navarro-Vazquez,A.Angew.Chem.,Int.Ed.2006,45,1966.
[55] Harmata,M.; Zheng,P.-G.; Schreiner,P.R.; Navarro-Vazquez,A.Tetrahedron Lett.2007,48,5919.
[56] Rama,D.A.; Iyengar,D.S.; Pardhasaradhi,M.Tetrahedron 1994,50,2543.
[57] de Faria,M.L.; Magalhaes,R.de A.; Silva,F.C.; Matias,L.G.de O.; Ceschi,M.A.; Brocksom,U.; Brocksom,T.J.Tetrahedron: Asymmetry 2000,11,4093.
[58] Akhmetvaleev,R.R.; Baibulatova,G.M.; Shavaleeva,G.A.; Miftakhov,M.S.Russ.J.Org.Chem.2001,37,243.
[59] Akhmetvaleev,R.R.; Baibulatova,G.M.; Imaeva,L.R.; Miftakhov,M.S.Russ.J.Org.Chem.2001,37,125.
[60] Mukai,C.; Kozaka,T.; Suzuki,Y.; Kim I.J.Tetrahedron 2004,60,2497.
[61] Davie,C.P.; Danheiser,R.L.Angew.Chem.,Int.Ed.2005,44,5867.
[62] Coquerel,Y.; Bremond,P.; Rodriguez,J.J.Organomet.Chem.2007,692,4805.
[63] Coquerel,Y.; Rodriguez,J.ARKIVOC 2008,227.
[64] Cunha,S.; Oliveira,C.C.; Sabino,J.R.J.Braz.Chem.Soc.2011,22,598.
[65] Xue,F.-L.M.S.Thesis,South China Normal University,Guangdong,2013 (in Chinese).(薛福玲,硕士论文,华南师范大学,广东,2013.)
[66] Rich,A.E.; DeGreeff,A.D.; McNeill,K.Chem.Commun.2002,234.
[67] Pratt,D.A.; van der Donk,W.A.J.Am.Chem.Soc.2005,127,384.
[68] Pratt,D.A.; van der Donk,W.A.Chem.Commun.2006,558.
[69] Lai,Y.-J.; Becker,J.G.Environ.Sci.Technol.2013,47,1518.
[70] Andersin,J.; Parkkinen,P.; Honkala,K.J.Catal.2012,290,118.

脱卤反应研究进展

Research Progress on Dehalogenation Reaction

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xiangping Chen, Chenxiang Meng, Mengna Li, Shangmin Chu, Xinxin Zhu, Kai Xu, Lantao Liu, Tao Wang, Fenghua Zhang, Fei Li. Fe-Catalyzed Synthesis of Sulfide-Based Aromatic Primary Amines in Water Promoted by Sodium-Ascorbate [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2800-2807.
[2]	Yang Han, Weichao Jiang, Jing Zhang, Jinsong Peng, Chunxia Chen. Visible-Light-Promoted Palladium-Catalyzed C—H Amination for the Synthesis of Carbazolequinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 266-276.
[3]	Honglei Jin, Fengxuan Jiang, Kai Cheng, Lehao Huang. Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides and Its Application to the Synthesis of the Core Sturctures of Aporphine and Aristolactam Alkaloids [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1691-1702.
[4]	Jin Jikang, Xia Huimin, Zhang Fenglian, Wang Yifeng. Lewis-Base Boryl Radicals Enabled Borylation, Radical Catalysis and Reduction Reactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2185-2194.
[5]	Wang Xucai, Chen Ming, Zhang Wei, Zhang Yaodu, Ren Zhihui, Guan Zhenghui. Palladium-Catalyzed 5-exo-trig Hydroamidation of β,γ-Unsaturated Hydrazones for Synthesis of Dihydropyrazoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1618-1624.
[6]	Li Xue, Song Zirui, Chen Xin, Cai Yichao, Liu Yajie, Chen Chunxia, Peng Jinsong. Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 950-958.
[7]	Ye Qingqing, Zhang Mengfan, Liu Yaozong, Yang Zhen. Synthesis of 3-Dehydroxyphomonol [J]. Chin. J. Org. Chem., 2019, 39(9): 2671-2675.
[8]	Xing Lihao, Shao Lingyan, Fu Xiaopan, Deng Kezuan, Yang Jinyue, Ji Yafei. Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp²)-H Bond Iodination Reaction [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3154-3161.
[9]	Yang Wencheng, Qi Xiaoxu, Chen Pinhong, Liu Guosheng. Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes [J]. Chin. J. Org. Chem., 2019, 39(1): 122-128.
[10]	Wu Yuqin, Yu Liangyun, Zhang Qi, Li Lidong. Synthesis of Dihydrophenanthridines by Palladium-Catalyzed[2+2+2] Cyclization Reactions [J]. Chin. J. Org. Chem., 2017, 37(9): 2336-2342.
[11]	Ullah Aziz, Zhang Sheng, Bao Ming. Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes [J]. Chin. J. Org. Chem., 2017, 37(5): 1278-1283.
[12]	Zhou Quanlong, Zhu Changlei, Wu Ge, Zhang Yuanfei, Zhang Min, Su Weiping. Construction of Carbazoles by Palladium-Catalyzed Direct Cross-Coupling of Indoles with in situ Generated Aryl Vinyl Ketones [J]. Chin. J. Org. Chem., 2017, 37(10): 2655-2662.
[13]	An Yanni, Li Jianxiao, Zhang Zhenming, Li Chunsheng, Yang Shaorong. Bromopalladation Triggering the Cascade Oxidative Heterocyclization Reaction of Alkynes with Alkenes in Ionic Liquids [J]. Chin. J. Org. Chem., 2016, 36(9): 2136-2141.
[14]	Cai Liangzhen, Lin Hui, Liu Taoping, Tao Xiaochun. Synthesis of Diarylaminofluorenes through Tandem Copper and Palladium Catalyzed Coupling-Cyclizing Reactions [J]. Chin. J. Org. Chem., 2015, 35(8): 1682-1690.
[15]	Wen Yanmei, Xie Jianying, Feng Runguang, Huang Xuming. Synthesis of 1,7-Diarylhepta-1,6-diyne Compounds [J]. Chin. J. Org. Chem., 2015, 35(3): 735-738.