综述与进展

还原型Heck反应的研究进展

  • 杨晓梅 ,
  • 马莎 ,
  • 杜艳妮 ,
  • 陶云海
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  • a 云南中医学院 昆明 650500;
    b 云南大学化学科学与工程学院 昆明 650091

收稿日期: 2013-03-31

  修回日期: 2013-05-20

  网络出版日期: 2013-06-04

基金资助

云南大学理(工)科校级科研(No. 2011YB12)及云南省教育厅基金(No. 2011Y112)资助项目.

Progress in Reductive Heck Reaction

  • Yang Xiaomei ,
  • Ma Sha ,
  • Du Yanni ,
  • Tao Yunhai
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  • a Yunnan University of Traditional Chinese Medicine, Kunming 650500;
    b School of Chemistry Science and Engineering, Yunnan University, Kunming 650091

Received date: 2013-03-31

  Revised date: 2013-05-20

  Online published: 2013-06-04

摘要

还原型Heck反应是不饱和卤代烃与烯烃在Heck反应条件下生成烯烃加成产物的偶联反应. 综述了三十年来还原型Heck反应的研究进展,对还原型Heck反应的方法和催化体系的组成、反应机理、应用和局限性等方面进行了介绍和评价.

本文引用格式

杨晓梅 , 马莎 , 杜艳妮 , 陶云海 . 还原型Heck反应的研究进展[J]. 有机化学, 2013 , 33(11) : 2325 -2333 . DOI: 10.6023/cjoc201303053

Abstract

Reductive Heck reaction is a coupling reaction which unsaturated halides react with olefinic compounds at the similar Heck conditions to form the addition products. In this paper, the progress in Heck coupling reaction including catalytic systems, mechanism, applications and limitation in organic chemistry is reviewed.

参考文献

[1] (a) Mizorold,T.; Mori,K.; Ozaki,A.Bull.Chem.Soc.1971,44,581.
(b) Heck,R.F.; Nolley,J.P.J.Org.Chem.1972,14,2320.
[2] (a) Cabri,W.; Candiani,I.Acc.Chem.Res.1995,28,2.
(b) Crisp,G.T.Chem.Soc.Rev.1998,27,427.
(c) Beletskaya,I.P.,Cheprakov,A.V.Chem.Rev.2000,100,3009.
[3] (a) Cacchi,S.; Arcadi,A.J.Org.Chem.1983,48,4236.
(b) Cacchi,S.; Palmieri,G.Tetrahedron 1983,39,3373.
(c) Cacchi,S.; Latorre,F.; Palmieri,G.J.Organomet.Chem.1984,268,c48.
(d) Amorese,A.; Arcadi,A.; Bernocchi,E.; Cacchi,S.; Cerrini,S.; Fedeli,W.; Ortar,G.Tetrahedron 1989,45,813.
(e) Cacchi,S.; Gasparrini,F.; Pace,P.; Villani,C.Synlett 2000,650.
[4] Gottumukkala,A.L.; Vries,J.G.; Minnaard,A.J.Chem.Eur.J.2011,17,3091.
[5] Hagiwara,H.; Eda,Y.; Morohashi,K.; Suzuki,T.; Ando,M.; Ito,N.Tetrahedron Lett.1998,39,4055.
[6] Fall,Y.; Doucet,H.; Santelli,M.Tetrahedron 2009,65,489.
[7] Soensen,U.S.; Bleisch,T.J.; Kingston,A.E.; Wright,R.A.; Johnson,B.G.; Schoepp,D.D.; Ornstein,P.L.Bioorg.Med.Chem.2003,11,197.
[8] Tobrman,T.; Dvorak,D.Tetrahedron Lett.2004,45,273.
[9] Namyslo,J.C.; Kaufmann,D.E.Chem.Ber.1997,130,1327.
[10] (a) Malpass,J.R.; Cox,C.D.Tetrahedron Lett.1999,40,1419.
(b) Cox,C.D.; Malpass,J.R.Tetrahedron 1999,55,11879.
(c) Malpass,J.R.; Hemmings,D.A.,Wallis,A.L.; Fletcher,S.R.; Patel,S.J.Chem.Soc.,Perkin Trans.1 2001,1044.
[11] (a) Dolci,L.; Dolle,F.; Valette,H.; Vaufrey,F.; Fuseau,C.; Bottlaender,M.; Crouzel,C.Bioorg.Med.Chem.1999,7,467.
(b) Wei,Z.L.; George,C.; Kozikowski,A.P.Tetrahedron Lett.2003,44,3847.
(c) Carroll,F.I.; Liang,F.; Navarro,H.A.; Brieaddy,L.E.; Abraham,P.; Damaj,M.I.; Martin,B.R.J.Med.Chem.2001,44,2229.
(d) Carroll,F.I.; Robinson,T.P.; Brieaddy,L.E.; Atkinson,R.N.; Mascarella,W.; Damaj,M.I.; Martin,B.R.; Navarro,H.A.J.Med.Chem.2007,50,6383.
(e) Kasyan,A.; Wagner,C.; Maier,M.E.Tetrahedron 1998,54,8047.
[12] (a) Celik,C.; Kulu,I.; Ocal,N.; Kaufmann,D.E.Helv.Chim.Acta 2009,92,1092.
(b) Kulu,I.; Ocal,N.Helv.Chim.Acta 2011,94,2054.
(c) Goksu,G.; Gul,M.; Ocal,N.; Kaufmann,D.E.Tetrahedron Lett.2008,49,2685.
[13] Asad,N.; Hanson,P.R.; Long,T.R.; Rayabarapu,D.K.; Rolfe,A.Chem.Commun.2011,47,9528.
[14] Wallberg,A.; Magnusson,G.Tetrahedron 2000,56,8533.
[15] Krow,G.R.; Yuan,J.; Huang,Q.; Meyer,M.D.; Anderson,D.J.; Campbellb,J.E.; Carroll,P.J.Tetrahedron 2000,56,9233.
[16] Wallace,D.J.; Goodman,J.M.; Kennedy,D.J.; Davies,A.J.; Cowden,C.J.; Ashwood,M.S.; Cottrell,I.F.; Dolling,U.; Reider,P.J.Org.Lett.2001,3,671.
[17] Friestad,G.K.; Branchaud,B.P.Tetrahedron Lett.1995,36,7047.
[18] Kim,H.S.; Lee,H.S.; Kim,S.H.; Kim,J.N.Tetrahedron Lett.2009,50,3154.
[19] Minatti,A.; Zheng,X.; Buchwald,S.L.J.Org.Chem.2007,72,9253.
[20] (a) Sole,D.; Bonjoch,J.; García-Rubio,S.; Peidro,E.; Bosch,J.Chem.Eur.J.2000,6,655.
(b) Sole,D.; Bonjoch,J.; García-Rubio,S.; Peidro,E.; Bosch,J.Angew.Chem.,Int.Ed.1999,38,395.
[21] Gao,P.; Cook,S.P.Org.Lett.2012,14,3340.
[22] Ichikawa,M.; Takahashi,M.; Aoyagi,S.; Kibayashi,C.J.Am.Chem.Soc.2004,126,16553.
[23] Brieaddy,L.E.; Mascarella,S.W.; Navarro,H.A.; Atkinson,R.N.; Damaj,M.I.; Martin,B.R.; Carroll,F.I.Tetrahedron Lett.2001,42,3795.
[24] (a) Jana,G.K.; Sinha,S.Tetrahedron 2012,68,7155.
(b) Jana,G.K.; Sinha,S.Tetrahedron Lett.2012,53,1671.
[25] (a) Pays,C.; Mangeney,P.Tetrahedron Lett.2001,42,589.
(b) Mangeney,P.; Pays,C.Tetrahedron Lett.2003,44,5719.
[26] Liu,P.; Huang,L.; Lu,Y.; Dilmeghani,M.; Baum,J.; Xiang,T.; Adams,J.; Tasker,A.; Larsen,R.; Faul,M.M.Tetrahedron Lett.2007,48,2307.
[27] Li,Z.; Watkins,E.B.; Liu,H.; Chittiboyina,A.G.; Carvalho,P.B.; Avery,M.A.J.Org.Chem.2008,73,7764.
[28] Fan,W.Y.; Wang,Z.L.; Li,H.C.; Fossey,J.S.; Deng,W.P.Chem.Commun.2011,47,2961.
[29] Peng,R.; Van Nieuwenhze,M.S.Org.Lett.2012,14,1962.
[30] Majumdar,K.C.; Ghosh,T.; Chakravorty,S.Tetrahedron Lett.2010,51,3372.
[31] Donets,P.A.; Eycken,E.V.V.Org.Lett.2007,9,3017.
[32] Ekebergh,A.; Borje,Anna.; Martensson,J.Org.Lett.2012,14,6274.
[33] (a) Geoghegan,K.; Kelleher,S.; Evans,P.J.Org.Chem.2011,76,2187.
(b) Kantam,M.L.; Chakravarti,R.; Chintareddy,V.R.; Sreedhar,B.; Bhargava,S.Adv.Synth.Catal.2008,350,2544.
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