On the catalytic activation of water-soluble NHC-Au(I) complexes by sonication and microwave irradiation: A comparative assessment

被引：5

作者：

Fernandez, Gabriela A. ^{[1
]}

Schiel, Maria A. ^{[1
]}

Silbestri, Gustavo F. ^{[1
]}

机构：

[1] Univ Nacl Sur UNS, Inst Quim INQUISUR, Dept Quim, CONICET, Av Alem 1253,B8000CPB, Bahia Blanca, Buenos Aires, Argentina

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2020年 / 923卷

关键词：

Aqueous reactions; Gold(I) complexes; Green chemistry; Homogeneous catalysis; Microwaves; Ultrasound; N-HETEROCYCLIC CARBENE; ABNORMAL NHC-GOLD(I) COMPLEXES; ULTRASOUND-ASSISTED SYNTHESIS; GOLD CATALYSIS; METAL-COMPLEXES; NHC COMPLEXES; HYDRATION; ALKYNES; TEMPERATURE; CHEMISTRY;

D O I：

10.1016/j.jorganchem.2020.121452

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Within the realm of sustainable chemistry and increasing demand for eco-compatible methods, this article describes our attempts to activate some water-soluble N-heterocyclic carbene (NHC)-based gold(I) complexes under two well-known and safe irradiation protocols: microwaves (MW) and ultrasound (US). A textbook reaction, alkyne hydration, was chosen to assess the performance of such activation protocols and their influence on the catalyst's ability to drive the reaction to completion. Reactions can easily be conducted in pure water or aqueous methanol (1:1). We show that sonication significantly enhances this transformation affording the product in higher yields and shorter reaction times than non-assisted reactions in water, while MW energy gives the desire product in quantitative yield in water:methanol after just 1 min. (C) 2020 Elsevier B.V. All rights reserved.

引用

页数：8

共 76 条

[1]

alvarez M B, 2015, SIGNPOST OPEN ACCESS, V3, P44

[2] Gold-catalysed reactions of diynes [J].

Asiri, Abdullah M. ;

Hashmi, A. Stephen K. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (16) :4471-4503

[3] Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis [J].

Baig, R. B. Nasir ;

Varma, Rajender S. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1559-1584

[4] Sulfonated Water-Soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-Transfer Agents to Platinum(II) [J].

Baquero, Edwin A. ;

Silbestri, Gustavo F. ;

Gomez-Sal, Pilar ;

Flores, Juan C. ;

de Jesus, Ernesto .

ORGANOMETALLICS, 2013, 32 (09) :2814-2826

[5] Organometallic gold(III) compounds as catalysts for the addition of water and methanol to terminal alkynes [J].

Casado, R ;

Contel, M ;

Laguna, M ;

Romero, P ;

Sanz, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11925-11935

[6] Gold(I) Complexes with Eight-Membered NHC Ligands: Synthesis, Structures and Catalytic Activity [J].

Cervantes-Reyes, Alejandro ;

Rominger, Frank ;

Rudolph, Matthias ;

Hashmi, A. Stephen K. .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (12) :2523-2533

[7] Sterically Demanding AgI and CuI N-Heterocyclic Carbene Complexes: Synthesis, Structures, Steric Parameters, and Catalytic Activity [J].

Cervantes-Reyes, Alejandro ;

Rominger, Frank ;

Hashmi, A. Stephen K. .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (24) :5530-5540

[8] Gold(I) Complexes Stabilized by Nine- and Ten-Membered N-Heterocyclic Carbene Ligands [J].

Cervantes-Reyes, Alejandro ;

Rominger, Frank ;

Rudolph, Matthias ;

Hashmi, A. Stephen K. .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (50) :11745-11757

[9] Power ultrasound in metal-assisted synthesis: From classical Barbier-like reactions to click chemistry [J].

Cintas, Pedro ;

Palmisano, Giovanni ;

Cravotto, Giancarlo .

ULTRASONICS SONOCHEMISTRY, 2011, 18 (04) :836-841

[10]

Cornils B, 2005, MULTIPHASE HOMOGENEOUS CATALYSIS, VOLS 1 AND 2, P1, DOI 10.1002/9783527619597

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