Water-Soluble Iridium N-Heterocyclic Carbene Complexes for the Alkylation of Amines with Alcohols

被引：29

作者：

Fernandes, Ana ^{[1
]}

Royo, Beatriz ^{[1
]}

机构：

[1] ITQB NOVA, Inst Tecnol Quim & Biol Antonio Xavier, Ave Republ 2, P-2780417 Oeiras, Portugal

来源：

CHEMCATCHEM | 2017年 / 9卷 / 20期

关键词：

alcohols; amines; carbenes; homogeneous catalysis; iridium; TRANSITION-METAL-COMPLEXES; ASTERISK-IR COMPLEXES; TRANSFER HYDROGENATION; PINCER COMPLEXES; CP-ASTERISK-IR(III) COMPLEXES; CATALYZED ALKYLATION; SELECTIVE ALKYLATION; STABLE CATALYSTS; LIGAND COMPLEXES; BOND ACTIVATION;

D O I：

10.1002/cctc.201700678

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 new series of water-soluble Ir complexes with N-heterocyclic carbene ligands that bear ester and amide groups has been obtained and fully characterized. The new complexes are highly reactive and selective for the alkylation of amines with alcohols with a 1:1 ratio of reactants in water and in the absence of base or other additives. The catalytic system has a broad substrate scope, which allows the synthesis of a variety of primary and secondary amines in excellent yields. A tolerance to a large range of functional groups was obtained.

引用

页码：3912 / 3917

页数：6

共 74 条

[31] New Water-Soluble Iridium(I)-N-Heterocyclic Carbene-Tertiary Phosphine Mixed-Ligand Complexes as Catalysts of Hydrogenation and Redox Isomerization [J].

Horvath, Henrietta ;

Katho, Agnes ;

Udvardy, Antal ;

Papp, Gabor ;

Szikszai, Dorina ;

Joo, Ferenc .

ORGANOMETALLICS, 2014, 33 (22) :6330-6340

[32]

Imm S., 2011, ANGEW CHEM, V123, P7741

[33] Improved Ruthenium-Catalyzed Amination of Alcohols with Ammonia: Synthesis of Diamines and Amino Esters [J].

Imm, Sebastian ;

Baehn, Sebastian ;

Zhang, Min ;

Neubert, Lorenz ;

Neumann, Helfried ;

Klasovsky, Florian ;

Pfeffer, Jan ;

Haas, Thomas ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7599-7603

[34] N-Alkylation of Amines with Alcohols Catalyzed by a Water-Soluble Cp*Iridium Complex: An Efficient Method for the Synthesis of Amines in Aqueous Media [J].

Kawahara, Ryoko ;

Fujita, Ken-ichi ;

Yamaguchi, Ryohei .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (07) :1161-1168

[35] Multialkylation of Aqueous Ammonia with Alcohols Catalyzed by Water-Soluble Cp*Ir-Ammine Complexes [J].

Kawahara, Ryoko ;

Fujita, Ken-ichi ;

Yamaguchi, Ryohei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15108-15111

[36]

Lalrempuia R., 2010, ANGEW CHEM, V122, p9959

[37] Water Oxidation Catalyzed by Strong Carbene-Type Donor-Ligand Complexes of Iridium [J].

Lalrempuia, Ralte ;

McDaniel, Neal D. ;

Mueller-Bunz, Helge ;

Bernhard, Stefan ;

Albrecht, Martin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) :9765-9768

[38] A Survey of the Borrowing Hydrogen Approach to the Synthesis of some Pharmaceutically Relevant Intermediates [J].

Leonard, John ;

Blacker, A. John ;

Marsden, Stephen P. ;

Jones, Martin F. ;

Mulholland, Keith R. ;

Newton, Rebecca .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (10) :1400-1410

[39] Water in N-Heterocyclic Carbene-Assisted Catalysis [J].

Levin, Efrat ;

Ivry, Elisa ;

Diesendruck, Charles E. ;

Lemcoff, N. Gabriel .

CHEMICAL REVIEWS, 2015, 115 (11) :4607-4692

[40] Selective N-monoalkylation of aromatic amines with benzylic alcohols by a hydrogen autotransfer process catalyzed by unmodified magnetite [J].

Martinez, Ricardo ;

Ramon, Diego J. ;

Yus, Miguel .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (10) :2176-2181

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