Preformed π-Allyl Iron Complexes as Potent, Well-Defined Catalysts for the Allylic Substitution

被引:77
作者
Holzwarth, Michael [1 ]
Dieskau, Andre [1 ]
Tabassam, Misbah [2 ]
Plietker, Bernd [1 ]
机构
[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
[2] Univ Punjab, Inst Chem, Lahore 54590, Pakistan
关键词
allyl ligands; homogeneous catalysis; iron; nucleophiles; regioselectivity; ALKYL-HALIDES; ENANTIOSELECTIVE ALLYLATION; NUCLEOPHILIC-SUBSTITUTION; GRIGNARD-REAGENTS; CARBON-HETEROATOM; AMINATION; REGIOSELECTIVITY; ALKYLATIONS; MOLYBDENUM; REACTIVITY;
D O I
10.1002/anie.200901930
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reanimation: Catalytically inactive π-allyl iron complexes are "reanimated" upon addition of N-heterocyclic carbene ligands such as 1,3-dimesitylimidazolin-2-ylidene (SIMES). A comparison of stoichiometric and catalytic allylic alkylation reactions shows the π-allyl mechanism to be active in this catalytic system. © 2009 Wiley-VCH Verlag GmbH & Co. KCaA.
引用
收藏
页码:7251 / 7255
页数:5
相关论文
共 101 条
[81]  
Spiess S., 2008, ANGEW CHEM, V120, P7764
[82]   Iridium-catalyzed asymmetric allylic substitutions -: Very high regioselectivity and air stability with a catalyst derived from dibenzo[a,e]cyclooctatetraene and a phosphoramidite [J].
Spiess, Stephanie ;
Welter, Carolin ;
Franck, Geraldine ;
Taquet, Jean-Philippe ;
Helmchen, Guenter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) :7652-7655
[83]   Iridium-catalyzed formation of carbon-carbon and carbon-heteroatom bonds [J].
Takeuchi, Ryo ;
Kezuka, Satoko .
SYNTHESIS-STUTTGART, 2006, (20) :3349-3366
[84]   VINYLATION OF GRIGNARD REAGENTS - CATALYSIS BY IRON [J].
TAMURA, M ;
KOCHI, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (06) :1487-&
[85]  
Trost B.M., 2000, Catalytic Asymmetric Synthesis II, P593
[86]  
Trost B.M., 2002, ANGEW CHEM INT EDIT, V114, P1101, DOI 3.0.CO
[87]  
2-2
[88]   Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles [J].
Trost, Barry M. ;
Zhang, Yong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) :14548-+
[89]   Asymmetric transition metal-catalyzed allylic alkylations [J].
Trost, BM ;
VanVranken, DL .
CHEMICAL REVIEWS, 1996, 96 (01) :395-422
[90]  
Trost BM, 2002, ANGEW CHEM INT EDIT, V41, P1059, DOI 10.1002/1521-3773(20020315)41:6<1059::AID-ANIE1059>3.0.CO