Regioselective C?H Alkylation of Anisoles with Olefins Catalyzed by Cationic Half-Sandwich Rare Earth Alkyl Complexes

被引:119
作者
Oyamada, Juzo [1 ,2 ]
Hou, Zhaomin [1 ,2 ]
机构
[1] RIKEN, Adv Sci Inst, Organometall Chem Lab, Wako, Saitama 3510198, Japan
[2] RIKEN, Adv Sci Inst, Adv Catalyst Res Team, Wako, Saitama 3510198, Japan
关键词
alkenes; alkylation; anisoles; C-H activation; rare-earth complexes; H BOND ACTIVATION; STYRENE-STYRENE SEQUENCES; CARBON-HYDROGEN BONDS; POLYMERIZATION CATALYSIS; AMINOBENZYL COMPLEXES; SCANDIUM; COPOLYMERIZATION; HYDROARYLATION; EFFICIENT; ARENES;
D O I
10.1002/anie.201206233
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A half sandwich helping: Cationic rare-earth alkyl species generated from half-sandwich rare-earth dialkyl complexes and [Ph3C][B(C 6F5)4] can serve as unique catalysts for the C-H regioselective alkylation of anisoles with alkenes. The reaction affords either ortho-monoalkylated derivatives or products substituted at the benzylic position, depending on the substrate chosen. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12828 / 12832
页数:5
相关论文
共 61 条
[1]  
[Anonymous], 2012, ANGEW CHE
[2]  
[Anonymous], 2011, ANGEW CHEM
[3]  
[Anonymous], ANGEW CHEM
[4]   C-H ACTIVATION OF ARENES AND SUBSTITUTED ARENES BY THE YTTRIUM HYDRIDE (CP-ASTERISK-2YH)2 - COMPETITION BETWEEN CP-ASTERISK LIGAND METALATION, ARENE METALATION, AND H/D EXCHANGE - MOLECULAR-STRUCTURES OF CP-ASTERISK-2Y(MU-H)(MU-ETA(1),ETA(5)-CH2C5ME4)YCP-ASTERISK AND CP-ASTERISK-2Y(O-C6H4PPH2CH2) [J].
BOOIJ, M ;
DEELMAN, BJ ;
DUCHATEAU, R ;
POSTMA, DS ;
MEETSMA, A ;
TEUBEN, JH .
ORGANOMETALLICS, 1993, 12 (09) :3531-3540
[5]   The Friedel-Crafts syntheses [J].
Calloway, NO .
CHEMICAL REVIEWS, 1935, 17 (03) :327-392
[6]   Highly efficient iodine-catalyzed hydroarylation of arenes with styrenes [J].
Chu, Cheng-Ming ;
Huang, Wan-Ju ;
Liu, Ju-Tsung ;
Yao, Ching-Fa .
TETRAHEDRON LETTERS, 2007, 48 (39) :6881-6885
[7]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[8]   Addition of the ortho-C-H bonds of phenol across an olefin catalysed by a chiral iridium(I) diphosphine complex [J].
Dorta, R ;
Togni, A .
CHEMICAL COMMUNICATIONS, 2003, (06) :760-761
[9]   Scandium, Yttrium, and Lanthanum Benzyl and Alkynyl Complexes with the N-(2-Pyrrolidin-1-ylethyl)-1,4-diazepan-6-amido Ligand: Synthesis, Characterization, and Z-Selective Catalytic Linear Dimerization of Phenylacetylenes [J].
Ge, Shaozhong ;
Meetsma, Auke ;
Hessen, Bart .
ORGANOMETALLICS, 2009, 28 (03) :719-726
[10]   Rare-Earth-Catalyzed C-H Bond Addition of Pyridines to Olefins [J].
Guan, Bing-Tao ;
Hou, Zhaomin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) :18086-18089