Construction of Heterobimetallic Catalytic Scaffold with a Carbene-Bipyridine Ligand: Gold-Zinc Two-Metal Catalysis for Intermolecular Addition of O-Nucleophiles to Nonactivated Alkynes

被引：12

作者：

Rawat, Vishal Kumar ^{[1
]}

Higashida, Kosuke ^{[1
]}

Sawamura, Masaya ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

来源：

ACS CATALYSIS | 2022年 / 12卷 / 14期

关键词：

gold catalysis; cooperative catalysis; heterobimetallic complex; nucleophilic addition; DFT calculation; N-HETEROCYCLIC CARBENE; CARBOXYLIC-ACIDS; GOLD(I)-CATALYZED ADDITION; BIMETALLIC CATALYSIS; INTERNAL ALKYNES; HYDROPHENOXYLATION; COMPLEXES; NHC; METAL; SCOPE;

D O I：

10.1021/acscatal.2c01701

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 gold(I) complex bearing an imidazo[1,5-a]pyridin-3-ylidene ligand with a 2,2'-bipyridine moiety at the C5 position was prepared as a template for constructing heterobimetallic cooperative catalysts. In situ generated gold-zinc bimetallic systems enabled intermolecular nucleophilic anti-addition of O-nucleophiles such as carboxylic acids and phenols toward nonactivated internal alkynes. DFT calculations supported the proposed cooperative action of the cationic gold atom and the zinc salt site for activating the alkyne and the carboxylic acid, respectively.

引用

页码：8325 / 8330

页数：6

共 40 条

[1] Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents [J].

Bertrand, Benoit ;

Citta, Anna ;

Franken, Inge L. ;

Picquet, Michel ;

Folda, Alessandra ;

Scalcon, Valeria ;

Rigobello, Maria Pia ;

Le Gendre, Pierre ;

Casini, Angela ;

Bodio, Ewen .

JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2015, 20 (06) :1005-1020

[2] Synthesis, Structures, and Biological Studies of Heterobimetallic Au(I)-Ru(II) Complexes Involving N-Heterocyclic Carbene-Based Multidentate Ligands [J].

Boselli, Luca ;

Carraz, Maelle ;

Mazeres, Serge ;

Paloque, Lucie ;

Gonzalez, German ;

Benoit-Vical, Francoise ;

Valentin, Alexis ;

Hemmert, Catherine ;

Gornitzka, Heinz .

ORGANOMETALLICS, 2015, 34 (06) :1046-1055

[3] Metal-Catalyzed Synthesis and Transformations of β-Haloenol Esters [J].

Cadierno, Victorio .

CATALYSTS, 2020, 10 (04)

[4] Regiospecific Acylation of Cycloplatinated Complexes: Scope, Limitations, and Mechanistic Implications [J].

Carroll, Jeffrey ;

Woolard, Hannah G. ;

Mroz, Robert ;

Nason, Charles A. ;

Huo, Shouquan .

ORGANOMETALLICS, 2016, 35 (09) :1313-1322

[5] Gold(I)-Catalyzed Addition of Carboxylic Acids to Alkynes [J].

Chary, Bathoju Chandra ;

Kim, Sunggak .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (22) :7928-7931

[6] Straightforward synthesis of [Au(NHC)X] (NHC = N-heterocyclic carbene, X = Cl, Br, I) complexes [J].

Collado, Alba ;

Gomez-Suarez, Adrian ;

Martin, Anthony R. ;

Slawin, Alexandra M. Z. ;

Nolan, Steven P. .

CHEMICAL COMMUNICATIONS, 2013, 49 (49) :5541-5543

[7] Au...H-C Hydrogen Bonds as Design Principle in Gold(I) Catalysis [J].

Darmandeh, Heidar ;

Loeffler, Julian ;

Tzouras, Nikolaos V. ;

Dereli, Busra ;

Scherpf, Thorsten ;

Feichtner, Kai-Stephan ;

Vanden Broeck, Sofie ;

Van Hecke, Kristof ;

Saab, Marina ;

Cazin, Catherine S. J. ;

Cavallo, Luigi ;

Nolan, Steven P. ;

Gessner, Viktoria H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (38) :21014-21024

[8] GENERAL-SYNTHESIS OF (Z)-ALK-1-EN-1-YL ESTERS VIA RUTHENIUM-CATALYZED ANTI-MARKOVNIKOV TRANS-ADDITION OF CARBOXYLIC-ACIDS TO TERMINAL ALKYNES [J].

DOUCET, H ;

MARTINVACA, B ;

BRUNEAU, C ;

DIXNEUF, PH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7247-7255

[9] Highly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes [J].

Dupuy, Stephanie ;

Gasperini, Danila ;

Nolan, Steven P. .

ACS Catalysis, 2015, 5 (11) :6918-6921

[10] Gold(I) Complexes with Ferrocenylphosphino Sulfonate Ligands: Synthesis and Application in the Catalytic Addition of Carboxylic Acids to Internal Alkynes in Water [J].

Francos, Javier ;

Esther Moreno-Narvaez, Maria ;

Cadierno, Victorio ;

Sierra, Diego ;

Ariz, Katherine ;

Gomez, Johana .

CATALYSTS, 2019, 9 (11)

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