Structure and Reactivity of Late Transition Metal η3-Benzyl Complexes

被引:116
作者
Trost, Barry M. [1 ]
Czabaniuk, Lara C. [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
基金
美国国家科学基金会;
关键词
asymmetric synthesis; homogeneous catalysis; crystallography; transition metals; eta(3)-coordination; CATALYZED NUCLEOPHILIC-SUBSTITUTION; CROSS-COUPLING REACTIONS; H BOND ACTIVATION; HALF-SANDWICH-TYPE; NONRIGID ORGANOMETALLIC MOLECULES; NUCLEAR-MAGNETIC-RESONANCE; PHASE-TRANSFER CATALYSIS; BENZYL HALIDES; OXIDATIVE ADDITION; CRYSTAL-STRUCTURE;
D O I
10.1002/anie.201305972
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The coordination of transition metals to organic fragments can yield complexes with fascinating and unexpected binding patterns. The study of metal-benzyl complexes has demonstrated the feasibility of eta(3)-coordination, which results in a dearomatized ring. These complexes also offer insight into reaction mechanisms as proposed intermediates in catalytic cycles. In this Review we discuss the synthesis and characterization of these complexes with late transition metals and the subsequent development of catalytic benzylic functionalization methods, including asymmetric variants.
引用
收藏
页码:2826 / 2851
页数:26
相关论文
共 226 条
[1]   Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877
[2]   Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C-H Bond Cleavages with Sulfamates or Phosphates as Electrophiles [J].
Ackermann, Lutz ;
Barfuesser, Sebastian ;
Pospech, Jola .
ORGANIC LETTERS, 2010, 12 (04) :724-726
[3]   Cationic η3-benzyl nickel compounds with diphosphine ligands as catalyst precursors for ethylene oligomerization/polymerization:: influence of the diphosphine bite angle [J].
Albers, I ;
Alvarez, E ;
Cámpora, J ;
Maya, CM ;
Palma, P ;
Sánchez, LJ ;
Passaglia, E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (04) :833-839
[4]   PHASE-TRANSFER CATALYZED ORGANOMETALLIC CHEMISTRY - COBALT CARBONYL-CATALYZED CARBONYLATION OF HALIDES [J].
ALPER, H ;
ABBAYES, HD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 134 (01) :C11-C14
[5]   Direct observation of noninnocent reactivity of ZnBr2 with alkyl halide complexes of nickel [J].
Anderson, TJ ;
Vicic, DA .
ORGANOMETALLICS, 2004, 23 (04) :623-625
[6]   DFT studies on the mechanism of allylative dearomatization catalyzed by palladium [J].
Ariafard, Alireza ;
Lin, Zhenyang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :13010-13016
[7]   Asymmetric palladium-catalyzed benzylic nucleophilic substitution:: high enantioselectivity with the DUPHOS family ligands [J].
Assié, M ;
Legros, JY ;
Fiaud, JC .
TETRAHEDRON-ASYMMETRY, 2005, 16 (06) :1183-1187
[8]   Enantiodivergence in alkylation of 1-(6-methoxynaphth-2-yl)ethyl acetate by potassium dimethyl malonate catalyzed by chiral palladium-DUPHOS complex [J].
Assie, Martine ;
Meddour, Abdelkrim ;
Fiaud, Jean-Claude ;
Legros, Jean-Yves .
TETRAHEDRON-ASYMMETRY, 2010, 21 (13-14) :1701-1708
[9]   AN INVESTIGATION OF THE PALLADIUM-CATALYZED, FORMATE-MEDIATED HYDROXYCARBONYLATION OF OPTICALLY-ACTIVE 1-ARYLETHYL ESTERS [J].
BAIRD, JM ;
KERN, JR ;
LEE, GR ;
MORGANS, DJ ;
SPARACINO, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1928-1933
[10]   Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions [J].
Bandgar, BP ;
Bettigeri, SV ;
Phopase, J .
TETRAHEDRON LETTERS, 2004, 45 (37) :6959-6962