中文
Earlier issues
Announcement
More
Progress in Chemistry 2010, Vol. 22 Issue (01): 58-70 Previous Articles   Next Articles

• Invited Article •

Transition Metal-Catalyzed Synthesis of Furan Derivatives

Lu Yuhua1; Song Feijie2; Jia Xueshun1**; Liu Yuanhong2**   

  1. (1. Department of Chemistry, Shanghai University, Shanghai 200444, China; 2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China)
  • Received: Revised: Online: Published:
  • Contact: Jia Xueshun;Liu Yuanhong E-mail:xsjia@mail.shu.edu.cn;yhliu@mail.sioc.ac.cn
  • Supported by:

    National Natural Science Foundation of China

PDF ( 2050 ) Cited
Export

EndNote

Ris

BibTeX

The furan rings constitute an important class of heterocycles, which behave not only as key structural subunits in numerous natural products, but also display wide range of bioactivities. They also have applications in medicine, agricultural chemicals and biological chemistry. This review focuses on the recent progress in transition metal-catalyzed synthesis of furan derivatives from acyclic precursors such as allenyl ketones, alkynones, (Z)-2-en-4-yn-1-ols (or -ones), alkynyl epoxides, 2-(1-alkynyl)-2-alken-1-ones. The research trend for the synthesis of furan derivatives is also prospected.

Contents
1 Introduction
2 Metal-catalyzed synthesis of furans
2.1 From allenyl ketones
2.2 From alkynones
2.3 From (Z)-2-en-4-yn-1-ols (or -ones)
2.4 From alkynyl epoxides
2.5 From 2-(1-alkynyl)-2-alkene-1-ones
2.6 Other methods
3 Conclusion and prospectives

Key words: transition metal, catalysis, furan, synthetic methods, acyclic precursors, cycloisomerization

CLC Number: 

[ 1 ] 　Heaney H, Ahn J S. Comp rehensive Heterocyclic Chemistry II( Eds. KatritzkyA R, Rees CW, Scriven E F V) , Oxford: Pergamon Press, 1996. Vol. 2, 297—436
[ 2 ] 　Kênig B. Science of Synthesis, Houben-Weyl Methods of Molecular Transformations ( Eds. Maas G) , Stuttgart, New York: Thieme, 2001. Vol. 9, 183—285
[ 3 ] 　The Chemistry of Heterocycles: Structure, Reactions, Syntheses,and Applications ( Eds. Eicher T, Haup tmann S) , Weinheim:Wiley-VCH, 2003. 52—62
[ 4 ] 　ElbandyM, Shinde P B, Dang H T, Hong J, Bae K S, Jung J H. J. Nat. Prod. , 2008, 71: 869—872
[ 5 ] 　Jadulco R, Proksch P, Wray V, Sudarsono B A, Gr? fe U. J.Nat. Prod. , 2001, 64: 527—530
[ 6 ] 　焦耳J A ( Joule J A) , 米尔斯K (Mills K)著. 由业诚(You Y C) , 高大彬(Gao D B) 等译. 杂环化学(Heterocyclic Chemistry) . 北京: 科学出版社(Beijing: Science Press) , 2004.335—361
[ 7 ] 　Lip shutz B H. Chem. Rev. , 1986, 86: 795—819
[ 8 ] 　MaierM. Organic Synthesis Highlights II ( Eds. Waldmann H) ,VCH: Weinheim, 1995. 231—242
[ 9 ] 　Benassi R. Comp rehensive Heterocyclic Chemistry II ( Eds. Katritzky A R, Rees C W, Scriven E F V ) . Oxford: Pergamon Press, 1996, Vol. 2, 259—295
[ 10 ] 　Gilchrist T L. J. Chem. Soc. Perkin Trans. 1, 1999,2849—2866
[ 11 ] 　Keay B A. Chem. Soc. Rev. , 1999, 28: 209—215
[ 12 ] 　Hou X L, Cheung H Y, Hon T Y, Kwan P L, Lo T H, Tong S Y, Wong H N C. Tetrahedron, 1998, 54: 1955—2020
[ 13 ] 　Lukevics E, Pudova O A. Chemistry of Heterocyclic Compounds,1997, 33: 133—154
[ 14 ] 　Friedrishsen W. Comprehensive Heterocyclic Chemistry II ( Eds.Katrizky A R, Rees C W, Scriven E F V ) , Pergamon: New York, 1996. Vol. 2, 351—393
[ 15 ] 　李林涛(Li L T) , 麻生明(Ma S M) . 有机化学(Organic Chemistry) , 2000, 20: 701—711
[ 16 ] 　Brown R C D. Angew. Chem. Int. Ed. , 2005, 44: 850—852
[ 17 ] 　Marshall J A, Robinson E D. J. Org. Chem. , 1990, 55:3450—3451
[ 18 ] 　Marshall J A, Wang X J. J. Org. Chem. , 1991, 56: 960—969
[ 19 ] 　Marshall J A, Bartley G S. J. Org. Chem. , 1994, 59: 7169—7171
[ 20 ] 　Marshall J A, Sehon C A. J. Org. Chem. , 1995, 60:5966—5968
[ 21 ] 　Hashmi A S K. Angew. Chem. Int. Ed. , 1995, 34:1581—1583
[ 22 ] 　Alcaide B, Almendros P, Campo TM. Eur. J. Org. Chem. ,2007, 72: 2844—2849
[ 23 ] 　Ma SM, Zhang J L. Chem. Commun. , 2000, 117—118
[ 24 ] 　Ma S M, Zhang J L, Lu L H. Chem. Eur. J. , 2003, 9:2447—2456
[ 25 ] 　Ma SM, Li L T. Org. Lett. , 2000, 2: 941—944
[ 26 ] 　Ma SM, Yu ZQ. Angew. Chem. Int. Ed. , 2002, 41: 1775—1778
[ 27 ] 　Ma SM, Yu Z Q. Chem. Eur. J. , 2004, 10: 2078—2087
[ 28 ] 　Ma SM, Gu Z H, Yu ZQ. J. Org. Chem. , 2005, 70: 6291—6294
[ 29 ] 　Sromek A W, Rubina M, Gevorgyan V. J. Am. Chem. Soc. ,2005, 127: 10500—10501
[ 30 ] 　Kim J T, Kel′in A V, Gevorgyan V. Angew. Chem. Int. Ed. ,2003, 42: 98—101
[ 31 ] 　Sromek A W, Kel′in A V, Gevorgyan V. Angew. Chem. Int.Ed. , 2004, 43: 2280—2282
[ 32 ] 　Dudnik A S, Gevorgyan V. Angew. Chem. Int. Ed. , 2007,46: 5195—5197
[ 33 ] 　Hashmi A S K, Schwarz L, Choi J H, Frost T M. Angew.Chem. Int. Ed. , 2000, 39: 2285—2288
[ 34 ] 　Baker R T, Nguyen P, Marder T B, Westcott S A. Angew.Chem. Int. Ed. , 1995, 34: 1336—1338
[ 35 ] 　Zhou C Y, Chan P W H, Che C M. Org. Lett. , 2006, 8:325—328
[ 36 ] 　Peng L L, Zhang X, Ma M, Wang J B. Angew. Chem. Int.Ed. , 2007, 46: 1905—1908
[ 37 ] 　Fukuda Y, Shiragami H, Utimoto K, Nozaki H. J. Org.Chem. , 1991, 56: 5816—5819
[ 38 ] 　Sheng H Y, Lin S Y, Huang Y Z. Synthesis, 1987,1022—1023
[ 39 ] 　Sniady A, Durharn A, MorrealeM S, Wheeler K A, Dembinski R. Org. Lett. , 2007, 9: 1175—1178
[ 40 ] 　Kel′in A V, Gevorgyan V. J. Org. Chem. , 2002, 67: 95—98
[ 41 ] 　Sheng H Y, Lin S Y, Hung Y Z. Tetrahedron Lett. , 1986, 27:4893—4894
[ 42 ] 　Dudnik A S, Sromek A W, Rubina M, Kim J T, Kel′in A V,Gevorgyan V. J. Am. Chem. Soc. , 2008, 130: 1440—1452
[ 43 ] 　Cadierno V, Gimeno J, Nebra N. Adv. Synth. Catal. , 2007,349: 382—394
[ 44 ] 　Zhan Z P , Wang S P, Cai X B, Liu H J, Yu J L, Cui Y Y.Adv. Synth. Catal. , 2007, 349: 2097—2102
[ 45 ] 　Imagawa H, Kurisaki T, Nishizawa M. Org. Lett. , 2004, 6:3679—3681
[ 46 ] 　Végh D, Zalup sky P, Kováˇc J. Synth. Commun. , 1990, 20:1113—1123
[ 47 ] 　Seiller B, Bruneau C, Dixneuf P H J. J. Chem. Soc. Chem.Commun. , 1994, 493—494
[ 48 ] 　Seiller B, Bruneau C, Dixneuf P H. Tetrahedron, 1995, 51 :13089—13102
[ 49 ] 　Kücükbay H, Cetinkaya B, Guesmi S, Dixneuf P H. Organometallics, 1996, 15: 2434—2439
[ 50 ] 　Gabriele B, Salerno G, Lauria E. J. Org. Chem. , 1999, 64:7687—7692
[ 51 ] 　Liu Y H, Song F J, Song Z Q, Liu M N, Yan B. Org. Lett. ,2005, 7: 5409—5412
[ 52 ] 　Du X W, Song F, Lu Y, Chen H, Liu Y H. Tetrahedron,2009, 65: 1839—1845
[ 53 ] 　Gabriele B, Salerno G, De Pascali F, CostaM, Chiusoli G P. J.Org. Chem. , 1999, 64: 7693—7699
[ 54 ] 　Bartolo G, Pierluigi P, Giuseppe S, Raffaella M. Synthesis,2006, 24: 4247—4251
[ 55 ] 　Díazlvarez A E, Crochet P, ZablockaM, Duhayon C, Cadierno V, Gimeno J, Majoralc J P. Adv. Synth. Catal. , 2006,348: 1671—1679
[ 56 ] 　; zdemir I, YiˇgitB, μetinkaya B, BlküD, TahirM N, Ar￥c￥C.J. Organomet. Chem. , 2001, 633: 27—32
[ 57 ] 　Miki K, Nishino F, Ohe K, Uemura S. J. Am. Chem. Soc. ,2002, 124: 5260—5261
[ 58 ] 　Miki K, Yokoi T, Nishino F, Kato Y, Washitake Y, Ohe K,Uemura S. J. Org. Chem. , 2004, 69: 1557—1564.
[ 59 ] 　McDonald F E, Schultzlb C C. J. Am. Chem. Soc. , 1994,116: 9363—9364
[ 60 ] 　Lo C Y, Guo H Y, Lian J J, Shen F M, Liu R S. J. Org.Chem. , 2002, 67: 3930—3932
[ 61 ] 　Aurrecoechea J M, Pérez E, SolayM. J. Org. Chem. , 2001,66 : 564—569
[ 62 ] 　Aurrecoechea J M, Pérez E. Tetrahedron, 2004, 60:4139—4149
[ 63 ] 　Hashmi A S K, Sinha P. Adv. Synth. Catal. , 2004, 346:432—438
[ 64 ] 　Shu X Z, Liu X Y, Xiao H Q, J i K G, Guo L N, Qi C Z, Liang YM. Adv. Synth. Catal. , 2007, 349: 2493—2498
[ 65 ] 　J i K G, Shen YW, Shu X Z, Xiao H Q, Bian Y J, Liang YM.Adv. Synth. Catal. , 2008, 350: 1275—1280
[ 66 ] 　Yao TL, Zhang X X, Larock R C. J. Am. Chem. Soc. , 2004,126: 11164—11165
[ 67 ] 　Patil N T, Wu H, Yamamoto Y. J. Org. Chem. , 2005, 70:4531—4534
[ 68 ] 　Oh C H, Reddy V R, Kim A, Rhim C Y. Tetrahedron Lett. ,2006, 47: 5307—5310
[ 69 ] 　Liu X Y, Pan Z L, Shu X Z, Duan X H, Liang YM. Synlett,2006, 1962—1964
[ 70 ] 　Xiao Y J, Zhang J L. Angew. Chem. Int. Ed. , 2008, 47:1903—1906
[ 71 ] 　Zhang J L, Schmalz H. Angew. Chem. Int. Ed. , 2006, 45:6704—6707
[ 72 ] 　Duan X H, Liu X Y, Guo L N, LiaoM C, LiuW M, Liang YM. J. Org. Chem. , 2005, 70: 6980—6983
[ 73 ] 　Karpov A S, Merkul E, Oeser T, Müller T J J. Chem. Commun. , 2005, 2581—2583
[ 74 ] 　SuhreM H, ReifM, Kirsch S F. Org. Lett. , 2005, 7: 3925—3927
[ 75 ] 　For aDFT study, see: Correa A, Marion N, Fensterbank L, MalacriaM, Nolan S P, Cavallo L. Angew. Chem. , Int. Ed. ,2008, 47: 718—721
[ 76 ] 　Zhang L M, Sun JW, Kozmin SA. Adv. Synth. Catal. , 2006,348: 2271—2296
[ 77 ] 　Marco2Contelles J, Soriano E. Chem. Eur. J. , 2007, 13:1350—1357
[ 78 ] 　Marion N, Nolan S P. Angew. Chem. Int. Ed. , 2007, 46:2750—2752
[ 79 ] 　Fürstner A, Davies P. Angew. Chem. Int. Ed. , 2007, 46:3410—3449
[ 80 ] 　Barluenga J, Riesgo L, Vicente R, López L A, TomásM. J.Am. Chem. Soc. , 2008, 130: 13528—13529
[ 81 ] 　Ma SM, Zhang J L. J. Am. Chem. Soc. , 2003, 125: 12386—12387
[ 82 ] 　Zhan L B, Guan Z H, Han Y, Xie Y X, He S, Liang YM. J.Org. Chem. , 2007, 72: 10276—10278
[ 83 ] 　Arcadi A, Cacchi S, Fabrizi G, Marinelli F, Parisi L M. Tetrahedron, 2003, 59: 4661—4671
[ 84 ] 　Yadav J S, Reddy B V S, SreenivasM, Satheesh G. Synthesis,2007, 11: 1712—1716
[ 85 ] 　Dey S, Nandi D, Pradhan P K, Giri V S, Jaisankar P. Tetrahedron Lett. , 2007, 48: 2573—2575
[ 86 ] 　Donohoe T J, Orr A J, Gosby K, Bingham M. Eur. J. Org.Chem. , 2005, 1969—1971
[ 87 ] 　Donohoe T J, Fishlock L P, Lacy A R, Procop iou P A. Org.Lett. , 2007, 9: 953—956
[ 88 ] 　Leclerc E, Tius M A. Org. Lett. , 2003, 5: 1171—1174
[ 89 ] 　Hashmi A S K, Schwarz L, Bolte M. Eur. J. Org. Chem. ,2004, 1923—1935
[ 90 ] 　Hayes S J, KnightD W, MenziesM D, O’HalloranM, TanW F. Tetrahedron Lett. , 2007, 48: 7709—7712
[ 91 ] 　Oh C H, Park H M, Park D I. Org. Lett. , 2007, 9:1191—1193
[ 92 ] 　Zhang D, Yuan C. Eur. J. Org. Chem. , 2007, 3916—3924
[1] Lan Mingyan, Zhang Xiuwu, Chu Hongyu, Wang Chongchen. MIL-101(Fe) and Its Composites for Catalytic Removal of Pollutants: Synthesis Strategies, Performances and Mechanisms [J]. Progress in Chemistry, 2023, 35(3): 458-474.
[2] Liu Yvfei, Zhang Mi, Lu Meng, Lan Yaqian. Covalent Organic Frameworks for Photocatalytic CO2 Reduction [J]. Progress in Chemistry, 2023, 35(3): 349-359.
[3] Kelong Fan, Lizeng Gao, Hui Wei, Bing Jiang, Daji Wang, Ruofei Zhang, Jiuyang He, Xiangqin Meng, Zhuoran Wang, Huizhen Fan, Tao Wen, Demin Duan, Lei Chen, Wei Jiang, Yu Lu, Bing Jiang, Yonghua Wei, Wei Li, Ye Yuan, Haijiao Dong, Lu Zhang, Chaoyi Hong, Zixia Zhang, Miaomiao Cheng, Xin Geng, Tongyang Hou, Yaxin Hou, Jianru Li, Guoheng Tang, Yue Zhao, Hanqing Zhao, Shuai Zhang, Jiaying Xie, Zijun Zhou, Jinsong Ren, Xinglu Huang, Xingfa Gao, Minmin Liang, Yu Zhang, Haiyan Xu, Xiaogang Qu, Xiyun Yan. Nanozymes [J]. Progress in Chemistry, 2023, 35(1): 1-87.
[4] Hao Chen, Xu Xu, Chaonan Jiao, Hao Yang, Jing Wang, Yinxian Peng. Fabrication of Multifunctional Core-Shell Structured Nanoreactors and Their Catalytic Performances [J]. Progress in Chemistry, 2022, 34(9): 1911-1934.
[5] Dang Zhang, Xi Wang, Lei Wang. Biomedical Applications of Enzyme-Powered Micro/Nanomotors [J]. Progress in Chemistry, 2022, 34(9): 2035-2050.
[6] Zhihua Gong, Sha Hu, Xueping Jin, Lei Yu, Yuanyuan Zhu, Shuangxi Gu. Synthetic Methods and Application of Phosphoester Prodrugs [J]. Progress in Chemistry, 2022, 34(9): 1972-1981.
[7] Bowen Xia, Bin Zhu, Jing Liu, Chunlin Chen, Jian Zhang. Synthesis of 2,5-Furandicarboxylic Acid by the Electrocatalytic Oxidation [J]. Progress in Chemistry, 2022, 34(8): 1661-1677.
[8] Huiyue Wang, Xin Hu, Yujing Hu, Ning Zhu, Kai Guo. Enzyme-Catalyzed Atom Transfer Radical Polymerization [J]. Progress in Chemistry, 2022, 34(8): 1796-1808.
[9] Ru Jiang, Chenxu Liu, Ping Yang, Shuli You. Condensed Matter Chemistry in Asymmetric Catalysis and Synthesis [J]. Progress in Chemistry, 2022, 34(7): 1537-1547.
[10] Xinglong Li, Yao Fu. Preparation of Furoic Acid by Oxidation of Furfural [J]. Progress in Chemistry, 2022, 34(6): 1263-1274.
[11] Xiaoqing Ma. Graphynes for Photocatalytic and Photoelectrochemical Applications [J]. Progress in Chemistry, 2022, 34(5): 1042-1060.
[12] Peng Wang, Huan Liu, Da Yang. Recent Advances on Tandem Hydroformylation of Olefins [J]. Progress in Chemistry, 2022, 34(5): 1076-1087.
[13] Xiaowei Li, Lei Zhang, Qixin Xing, Jinyu Zan, Jin Zhou, Shuping Zhuo. Construction of Magnetic NiFe2O4-Based Composite Materials and Their Applications in Photocatalysis [J]. Progress in Chemistry, 2022, 34(4): 950-962.
[14] Fengshou Yu, Jiayu Zhan, Lu-Hua Zhang. The progress on Electrochemical CO2-to-Formate Conversion by p-Block Metal Based Catalysts [J]. Progress in Chemistry, 2022, 34(4): 983-991.
[15] Hao Sun, Chaopeng Wang, Jun Yin, Jian Zhu. Fabrication of Electrocatalytic Electrodes for Oxygen Evolution Reaction [J]. Progress in Chemistry, 2022, 34(3): 519-532.