Iridium-catalyzed benzylic C-H activation and functionalization of alkyl arenes

被引:17
作者
Voutchkova, Adelina M. [1 ]
Crabtree, Robert H. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
Iridium; C-H functionalization; Heterogeneous catalysis; Imine; Amine; DEHYDROGENATIVE-COUPLING CDC; BOND ACTIVATION; NITROGEN ATOM; ARYLATION; ADJACENT; SP(2); MECHANISM; TETRAHYDROISOQUINOLINES; COMPLEXES; INSERTION;
D O I
10.1016/j.molcata.2009.07.019
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A recyclable catalyst, Ir/C. gives C-H benzylic functionalization of simple arenes to afford aldehydes, esters, and imines. In the case of esters, an additive, Ag2CO3. acts as base and oxidant, while for imine formation no additive is necessary. In this latter case a double C-H activation is proposed. accompanied by loss of H-2. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:1 / 6
页数:6
相关论文
共 51 条
[1]   C-H activation of substituted arenes by tungsten alkylidene complexes: Products, selectivity, and mechanism [J].
Adams, CS ;
Legzdins, P ;
Tran, E .
ORGANOMETALLICS, 2002, 21 (07) :1474-1486
[2]   Intermolecular hydroamination of vinyl arenes using tungstophosphoric acid as a simple and efficient catalyst [J].
Babu, N. Seshu ;
Reddy, K. Mohan ;
Prasad, P. S. Sai ;
Suryanarayana, I. ;
Lingaiah, N. .
TETRAHEDRON LETTERS, 2007, 48 (43) :7642-7645
[3]   Intermolecular oxidative enolate heterocoupling [J].
Baran, Phil S. ;
DeMartino, Michael P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :7083-7086
[4]   Copper catalyzed oxidative alkylation of sp3 C-H bond adjacent to a nitrogen atom using molecular oxygen in water [J].
Basle, Olivier ;
Li, Chao-Jun .
GREEN CHEMISTRY, 2007, 9 (10) :1047-1050
[5]   Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds [J].
Borduas, Nadine ;
Powell, David A. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7822-7825
[6]   Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].
Campeau, Louis-Charles ;
Schipper, Derek J. ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+
[7]   Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes [J].
Chatani, N ;
Asaumi, T ;
Yorimitsu, S ;
Ikeda, T ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10935-10941
[8]   TAUTOMERISM OF ARENE AND DITERTIARY PHOSPHINE COMPLEXES OF RUTHENIUM(O) AND PREPARATION OF NEW TYPES OF HYDRIDOCOMPLEXES OF RUTHENIUM(2) [J].
CHATT, J ;
DAVIDSON, JM .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (FEB) :843-&
[9]   Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways [J].
Chen, Xiao ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12634-12635
[10]   Validation of the M-C/H-C bond enthalpy relationship through application of density functional theory [J].
Clot, Eric ;
Megret, Claire ;
Eisenstein, Odile ;
Perutz, Robin N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (25) :8350-8357