Synthesis of Carbene-Metal-Amido (CMA) Complexes and Their Use as Precatalysts for the Activator-Free, Gold-Catalyzed Addition of Carboxylic Acids to Alkynes

被引：10

作者：

Hashim, Ishfaq Ibni ^{[1
,2
]}

Tzouras, Nikolaos, V ^{[1
,2
]}

Janssens, Wim ^{[1
,2
]}

Scattolin, Thomas ^{[3
]}

Bourda, Laurens ^{[1
,2
]}

Bhandary, Subhrajyoti ^{[1
,2
]}

Van Hecke, Kristof ^{[1
,2
]}

Nolan, Steven P. ^{[1
,2
]}

Cazin, Catherine S. J. ^{[1
,2
]}

机构：

[1] Univ Ghent, Dept Chem, Krijgslaan 281,S-3, B-9000 Ghent, Belgium

[2] Univ Ghent, Ctr Sustainable Chem, Krijgslaan 281,S-3, B-9000 Ghent, Belgium

[3] Univ Padua, Dipartimento Sci Chim, Via Marzolo 1, I-35131 Padua, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 47期

关键词：

alkynes; BIAN-NHC; carbene-metal-amido; carboxylic acids; gold; N-heterocyclic carbene complexes; INTERNAL ALKYNES; GOLD(I)-CATALYZED ADDITION; LIGANDS SYNTHESIS; ACETYLENIC ACIDS; SILVER-FREE; EFFICIENT; CYCLOISOMERIZATION; REACTIVITY; COPPER; HYDROCARBOXYLATION;

D O I：

10.1002/chem.202201224

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A straightforward synthetic protocol leading to carbene-metal-amido (CMA) complexes (metal=Au, Cu) using a mild base and an environmentally desirable solvent (EtOH) has been explored, with a focus on complexes bearing backbone-substituted N-heterocyclic carbene (NHC) ligands, including BIAN-NHCs (BIAN=bis(imino)acenaphthene). The novel CMAs were structurally characterized, and gold-based CMAs bearing diverse NHCs were screened as simple, Bronsted-basic precatalysts. The readily accessible complexes display high catalytic activity in the intermolecular and intramolecular hydrocarboxylation of internal alkynes and alkynoic acids respectively, while the screening reveals the ancillary ligand effect of NHCs in these catalytic systems.

引用

页数：7

共 3 条

[1] Gold-Catalyzed Addition of Carboxylic Acids to Alkynes and Allenes: Valuable Tools for Organic Synthesis
Cadierno, Victorio
CATALYSTS, 2020, 10 (10) : 1 - 37
[2] Gold(I) Complexes with Ferrocenylphosphino Sulfonate Ligands: Synthesis and Application in the Catalytic Addition of Carboxylic Acids to Internal Alkynes in Water
Francos, Javier
Esther Moreno-Narvaez, Maria
Cadierno, Victorio
Sierra, Diego
Ariz, Katherine
Gomez, Johana
CATALYSTS, 2019, 9 (11)
[3] One-Pot and Regioselective Gold-Catalyzed Synthesis of 2-Imidazolyl-1-pyrazolylbenzenes from 1-Propargyl-1H-benzotriazoles, Alkynes and Nitriles through -Imino Gold(I) Carbene Complexes
Gonzalez, Jairo
Santamaria, Javier
Suarez-Sobrino, Angel L.
Ballesteros, Alfredo
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (09) : 1398 - 1403

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