Dehydrogenative Oxidation of Alcohols in Aqueous Media Catalyzed by a Water-Soluble Dicationic Iridium Complex Bearing a Functional N-Heterocyclic Carbene Ligand without Using Base

被引：144

作者：

Fujita, Ken-ichi ^{[1
]}

Tamura, Ryuichi ^{[1
]}

Tanaka, Yuhi ^{[1
]}

Yoshida, Masato ^{[1
]}

Onoda, Mitsuki ^{[1
]}

Yamaguchi, Ryohei ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Human & Environm Studies, Sakyo Ku, Kyoto 6068501, Japan

来源：

ACS CATALYSIS | 2017年 / 7卷 / 10期

关键词：

dehydrogenation; iridium catalyst; functional ligand; N-heterocyclic carbene; alcohol; ketone; carboxylic acid; CARBOXYLIC-ACID SALTS; ORGANIC-REACTIONS; ACCEPTORLESS DEHYDROGENATION; BIPYRIDONATE LIGAND; BIPYRIDINE LIGAND; HYDROGENATION; CONVERSION; SYSTEM; AMINES; GREEN;

D O I：

10.1021/acscatal.7b02560

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 dicationic iridium complex bearing a bidentate ligand that comprises N-heterocyclic carbene and a-hydroxypyridine moieties has been designed and synthesized. The complex exhibited high catalytic performance in aqueous media for the dehydrogenative oxidation of secondary alcohols to ketones accompanying the evolution of hydrogen. Furthermore, dehydrogenative transformation of primary alcohols to the carboxylic acids in aqueous media was also catalyzed by the complex without using base.

引用

页码：7226 / 7230

页数：5

共 46 条

[1]

Balaraman E, 2013, NAT CHEM, V5, P122, DOI [10.1038/NCHEM.1536, 10.1038/nchem.1536]

[2] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].

Butler, Richard N. ;

Coyne, Anthony G. .

CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337

[3]

Cazin CSJ, 2011, CATAL MET COMPLEXES, V32, P1, DOI 10.1007/978-90-481-2866-2

[4] Organic Synthesis "On Water" [J].

Chanda, Arani ;

Fokin, Valery V. .

CHEMICAL REVIEWS, 2009, 109 (02) :725-748

[5] Rhodium and iridium complexes of N-heterocyclic carbenes via transmetalation: Structure and dynamics [J].

Chianese, AR ;

Li, XW ;

Janzen, MC ;

Faller, JW ;

Crabtree, RH .

ORGANOMETALLICS, 2003, 22 (08) :1663-1667

[6] Selective conversion of alcohols in water to carboxylic acids by in situ generated ruthenium trans dihydrido carbonyl PNP complexes [J].

Choi, Jong-Hoo ;

Heim, Leo E. ;

Ahrens, Mike ;

Prechtl, Martin H. G. .

DALTON TRANSACTIONS, 2014, 43 (46) :17248-17254

[7] Stability and reactivity of N-heterocyclic carbene complexes [J].

Crudden, CM ;

Allen, DP .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2247-2273

[8]

DiezGonzalez S, 2011, RSC CATAL SER, P1

[9] Ionic Liquid-Promoted Oxidant-Free Dehydrogenation of Alcohols with Water-Soluble Ruthenium Nanoparticles in Aqueous Phase [J].

Feng, Bo ;

Chen, Chen ;

Yang, Hanmin ;

Zhao, Xiuge ;

Hua, Li ;

Yu, Yinyin ;

Cao, Ting ;

Shi, Yu ;

Hou, Zhenshan .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (08) :1559-1565

[10] Ligand-promoted dehydrogenation of alcohols catalyzed by Cp*Ir complexes. A new catalytic system for oxidant-free oxidation of alcohols [J].

Fujita, Ken-ichi ;

Tanino, Nobuhide ;

Yamaguchi, Ryohei .

ORGANIC LETTERS, 2007, 9 (01) :109-111

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