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Progress in Chemistry 2005, Vol. 17 Issue (02): 286-292 Previous Articles   Next Articles

• Review •

Progress in Palladium??Catalyzed Amination of Aryl Halides

Liu Pu *   Li Sanhua    Li Limin    Wang Xiangyu  Yin Yuanqi    Zhang Yuhua   

  1. (1。 Department of Chemistry, Zhengzhou University, Zhengzhou 450052, China;2.Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China)
  • Received: Revised: Online: Published:
  • Contact: Liu Pu E-mail:liupu@ zzu. edu. cn
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It is an important method to form CAr ?? N by palladium??catalyzed amination of aryl halides. The develop?? ment of ligands expands the scope of substrates, improves reaction selectivity and realizes the amination of the cheaper and available aryl chlorides. The applicat ion of weak base improves the compatibility of functional groups. Pd??catalyzed aminat ion of aryl halides are used in the synthesis of arylamine. The research progress in palladium??catalyzed amination is reviewed and prospected by using aryl halides as clue.

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[ 1 ] Hartwig J F. Angew. Chem. Int . Ed. Engl . , 1998 , 37 : 2046 —2067
[ 2 ] Beilfeid A J , Brown G R , Fobiser A J . Tetrahadron , 1999 , 55 :11399 —11428
[ 3 ] Yang B H , Buchwald S L. J . Organomet . Chem. , 1999 , 576 :125 —146
[ 4 ] 张贞发(Zhang Z F) , 周伟澄(Zhou W C) . 有机化学(Chinese Journal of Organic Chemisty) , 2002 , 22 : 685 —693
[ 5 ] Kosugi M L , Ameyama M, Migita T. Chem. Lett . , 1983 : 927 —928
[ 6 ] Paul F , Patt J , Hartwig J F. J . Am. Chem. Soc. , 1994 , 116 :5969 —5970
[ 7 ] Guram A S , Rennels R A , Buchwald S L. Angew. Chem. Int .Ed. Engl . , 1995 , 34 : 1348 —1350
[ 8 ] Wolf J P , Wagaw S , Buchwald S L. J . Am. Chem. Soc. , 1996 ,118 : 7215 —7217
[ 9 ] Guari Y, Vanes D S , Reek J N H , et al . Tetrahedron Lett . ,1999 , 40 : 3789 —3790
[10] Artamkina G A , Sergeev A G, Beletskaya I P. Tetrahedron Lett . ,2001 , 42 : 4381 —4384
[11] Driver M S , Hartwig J F. J . Am. Chem. Soc. , 1996 , 118 :7217 —7218
[12] Mann G, Hartwig J F. Drive M S , et al . J . Am. Chem. Soc. ,1998 , 120 : 827 —828
[13] Gabriela A G, Mihais S V , Huang J K, et al . J . Org. Chem. ,2001 , 66 : 7729 —7737
[14] Marinetti A , Hubert P , Genrt J P. Eur. J . Org. Chem. , 2000 :1815 —1820
[15] Harris M C , Geis O , Buchwald SL. J . Org. Chem. , 1999 , 64 :6019 —6022
[16] Prashad M, Mak X Y, Liu Y G, et al . J . Org. Chem. , 2003 ,68 : 1163 —1164
[17] Sadighl J P , Harris M C , Buchwald S L. Tetrahedron Lett . ,1998 , 39 : 5327 —5330
[18] Urgaonkar S , Nagarajian M, Verkand J G. Org. Lett . , 2003 , 5 :815 —818
[19] Wolf P , Buchwald S L. J . Org. Chem. , 1997 , 62 : 6066 —6068
[20] Hartwig J F , Kawatsura M, Hauck S I. J . Am. Chem. Soc. ,1999 , 64 : 5575 —5580
[21] Stambuli J P , Buehl M, Hartwig J F. J . Am. Chem. Soc. ,2002 , 124 : 9346 —9347
[22] Wolf J P , Buchwald S L. J . Am. Chem. Soc. , 2000 , 65 :1144 —1157
[23] Harris M C , Huang X H , Buchwald S L. Org. Lett . , 2002 , 4 :2885 —2888
[24] Basu B , Satadru J , Mridha N K, et al . Tetrahedron Lett . , 2002 ,43 : 7967 —7969
[25] Wan Y Q , Alterman M, HallBerg A. Synthesis2Stuttgart , 2002 ,(11) : 1597 —1600
[26] Wang T , Magnin D R , Hamann L G. Org. Lett . , 2003 , 5 :897 —900
[27] Beller M, Riermeiner T H , Reisinger C P , et al . Tetrahedron Lett . , 1997 , 38 : 2073 —2074
[28] Reddy N P , Tanaka M. Tetrahedron Lett . , 1997 , 38 : 4807 —4810
[29] Hamann B C , Hartwig J F. J . Am. Chem. Soc. , 1998 , 120 :7369 —7370
[30] Bei X, Guram A S , Turner H W. Tetrahedron Lett . , 1999 , 40 :1237 —1240
[31] Kataoka N , Shelby Q , Stambuli J P , et al . J . Org. Chem. ,2002 , 67 : 5553 —5566
[32] Old D W, Wolf J P , Buchwald S L. J . Am. Chem. Soc. , 1998 ,120 : 9722 —9723
[33] Brown J A. Tetrahedron Lett . , 2000 , 41 : 1623 —1626
[34] Viciu M S , Kissing R M, Steven E D , et al . Org. Lett . , 2002 ,4 : 2229 —2231
[35] Kim Y M, Yu S. J . Am. Chem. Soc. , 2003 , 125 : 1696 —1697
[36] Wolfe J P , Ahman J , Sadighi J P , et al . Tetrahedron Lett . ,1997 , 38 : 6367 —6370
[37] Jaime-Figueroa S , Liu Y, Muchowski J M, et al . Tetrahedron Lett . , 1998 , 39 : 1313 —1316
[38] Hori K, Mori M. J . Am. Chem. Soc. , 1998 , 120 : 7651 —7652
[39] Huang X H , Buchwald S L. Org. Lett . , 2001 , 3 : 3417 —3419
[40] Willoughby C A , Chapman K T. Tetrahedron Lett . , 1996 , 37 :7181 —7184
[41] Ward Y D , Farina V. Tetrahedron Lett . , 1996 , 37 : 6993 —6996
[42] Weigand K, Pelka S. Org. Lett . , 2002 , 4 : 4689 —4692
[43] Reetz M T , Westermann E. Angew. Chem. Int . Ed. Engl . ,2000 , 39 : 165 —167
[44] Vladimir K, Zeev A , Ronit P B , et al . Org. Lett . , 2002 , 4 :3529 —3532
[45] Lipschutz B H , Veda H. Angew. Chem. Int . Ed. Engl . , 2000 ,39 : 4492 —4494
[46] Gujadhur R , Venkatarman D , Kintigh J T. Tetrahedron Lett . ,2001 , 42 : 4791 —4793
[47] Sasaki M, Dalili S , Yudin A K. J . Org. Chem. , 2003 , 8 :2045 —2047
[48] Amatore C , Broeker G, Jutand A , Khalil F. J . Am. Chem.Soc. , 1997 , 119 : 5176 —5185
[49] Singh U K, Strieter E R , Blackmond D G, et al . J . Am. Chem.Soc. , 2002 , 124 : 14104 —14114

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