中文
Announcement
More
Progress in Chemistry 2010, Vol. 22 Issue (07): 1233-1241 Previous Articles   Next Articles

• Invited Article •

Organic Reactions "on Water"

Liu Li**    Wang Dong   

  1. (CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China)
  • Received: Online: Published:
PDF ( 3298 ) Cited
Export

EndNote

Ris

BibTeX

The development of “on water” organic reaction is a breakthrough in the field of aqueous organic reactions for green synthesis. An essential characteristic of “on water” reaction is heterogeneity of the reaction system. Water is not only used as a green reaction media, but also, in most “on water” reactions, plays a crucial role in observing large rate acceleration and selectivity enhancement. Under “on water” reaction conditions, the reaction can be scaled-up and the procedure is favorable to make a clear phase separation. The recent advancements of “on water”organic reaction and its applications in green organic synthesis are reviewed in terms of classification of organic reaction.

Contents 
1 Introduction 
2 Cycloaddition reaction on water 
3 Nucleophilic addition reaction on water 
3.1 Conjugate addition 
3.2 Nucleophilic addition to carbonyl groups 
3.3 Au-catalyzed tandem reaction 
3.4 Enantioselective direct aldol reaction 
4 Nucleophilic substitution reaction on water 
5 Coupling reaction on water 
5.1 Transition metal-catalyzed coupling reaction 
5.2 Dehydrogenative coupling reaction 
6 Oxidation on water 
7 Bromination reaction on water 
8 Theoretical studies 
9 Conclusion

CLC Number: 

[1 ] Grieco A. Organic Synthesis in Water. London: Black Academic
& Professional,1998
[2 ] Li C J,Chan T H. Comprehansive Organic Reaction in Aqueous
Media. NY: John Wiley & Sons,Inc. Hoboken,2007
[3 ] Rideout D C,Breslow R. J. Am. Chem. Soc. ,1980,102:
7816—7817
[4 ] Narayan S,Muldoon J,Finn M G,Fokin V V,Kolbe H C,
Sharpless K B. Angew. Chem. Int. Ed. ,2005,44: 3275—
3279
[5 ] Chanda A,Fokin V V. Chem. Rev. ,2009,109: 725—748
[6 ] González-Cruz D,Tejedor D,de Armas P,García-Tellado F.
Chem. Eur. J. ,2007,13: 4823—4832
[7 ] González-Cruz D, Tejedor D, de Armas P, Moralesa E Q,
García-Tellado F. Chem. Commun. ,2006,2798—2800
[8 ] Ranu B C,Banerjee S. Tetrahedron Lett. ,2007,48: 141—143
[9 ] Zheng Z,Perkin B L,Ni B. J. Am. Chem. Soc. ,2010,132:
50—51
[10] Kumaravel K,Vasuki G. Green Chem. ,2009,11: 1945—1947
[11] Shaabani A,Rahmati A,Farhangi E. Tetrahedron Lett. ,2007,
48: 7291—7294
[12] Chakraborti A K, Rudrawar S, Jadhav K B, Kaur G,
Chankeshwara S V. Green Chem. ,2007,9: 1335—1340
[13] Liu X Y,Che C M. Angew. Chem. Int. Ed. ,2008,47:
3805—3810
[14] Guizzetti S,Benaglia M,Raimondi L,Celentano G. Org. Lett. ,
2007,9: 1247—1250
[15] Huang J,Zhang X,Armstrong D W. Angew. Chem. Int. Ed. ,
2007,46: 9073—9077
[16] Cozzi P G,Zoli L. Green Chem. ,2007,9: 1292—1295
[17] Cozzi P G,Zoli L. Angew. Chem. Int. Ed. ,2008,47: 4162—
4166
[18] Fleckenstein C A,Plenio H. Green Chem. ,2007,9: 1287—
1291
[19] Turner G L,Morris J A,Greaney M F. Angew. Chem. Int.
Ed. ,2007,46: 7996—8000
[20] Carril M,SanMartin R,Tellitu I,Domínguez E. Org. Lett. ,
2006,8: 1467—1470
[21] Wei C M,Li C J. J. Am. Chem. Soc. ,2003,125: 9584—
9585
[22] Chung L L,Yang J,Wei Y,Ying J Y. Adv. Synth. Catal. ,
2009,351: 2887—2896
[23] Huang B S,Yao X Q,Li C J. Adv. Synth. Catal. ,2006,348:
1528—1532
[24] Yan B,Liu Y. Org. Lett. ,2007,9: 4323—4326
[25] Zhang H B,Liu L,Chen Y J,Wang D,Li C J. Eur. J. Org.
Chem. ,2006,869—873
[26] Zhang H B,Liu L,Chen Y J,Wang D,Li C J. Adv. Synth.
Catal. ,2006,348: 229—235
[27] Wallis P J,Booth K J,Pattiab A F,Scott J L. Green Chem. ,
2006,8: 333—337
[28] Li H J,Zhao J L,Chen Y J,Liu L,Wang D,Li C J. Green.
Chem. ,2005,7: 61—63
[29] Shapiro N,Vigalok A. Angew. Chem. Int. Ed. ,2008,47:
2849—2852
[30] Pirrung M C,Das Sarma K. J. Am. Chem. Soc. ,2004,126:
444—445
[31] Podgorek A,Stavber S,Zupanb M,Iskra J. Tetrahedron Lett. ,
2006,47: 1097—1099
[32] Podgorek A,Stavber S,Zupanab M,Iskra J. Green Chem. ,
2007,9: 1212—1218
[33] Pirrung M C. Chem. Eur. J. ,2006,12: 1312—1317
[34] Jung Y,Marcus R A. J. Am. Chem. Soc. ,2007,129: 5492—
5502

[1] Zhu Yingguang, Di Changwei, Hu Wenhao. Asymmetric Multicomponent Reactions [J]. Progress in Chemistry, 2010, 22(07): 1380-1396.
[2] Wang Qifang Song Xiaokai Yan Chaoguo. Application of Malononitrile in Multicomponent Reactions [J]. Progress in Chemistry, 2009, 21(05): 997-1007.
[3] Ai-You Hao Zhang Hua-Cheng Jian Shen. The Application of Cyclodextrins in Greeen Organic Synthesis [J]. Progress in Chemistry, 2008, 20(11): 1694-1698.
Viewed
Full text


Abstract

Organic Reactions "on Water"