Phosphine-Based Hyper-Cross-Linked Polymer-Supported Neutral Gold(I) Complex as a Recyclable Catalyst for the Regioselective Hydration of Alkynes to Ketones

被引：4

作者：

Shen, Lu ^{[1
]}

Han, Xingyou ^{[1
]}

Dong, Beixuan ^{[1
]}

Yang, Yong ^{[1
]}

Yang, Jiazhi ^{[1
]}

Li, Feng ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem & Chem Engn, Nanjing 210094, Peoples R China

来源：

ACS APPLIED POLYMER MATERIALS | 2022年 / 4卷 / 10期

关键词：

hyper-cross-linked polymers; neutral gold(I) complex; hydration of alkynes; regioselective; recyclable catalyst; phosplwic ligand; FORMAL TOTAL-SYNTHESIS; TERMINAL ALKYNES; N-METHYLATION; ALCOHOLS; METHANOL; WATER; ACID; TRANSFORMATION; HYDROGENATION; ACTINORANONE;

D O I：

10.1021/acsapm.2c01167

中图分类号：

T [工业技术];

学科分类号：

08 ;

摘要：

Functionalized hyper-cross-linked polymer-supported metal complexes have been developed as heterogeneous catalysts for organic synthesis and have attracted much attention. In this regard, a phosphine-based hyper-cross-linked polymersupported neutral gold(I) complex, Au@HCPs-PPh3, which is synthesized by incorporation of [(Me2S)AuCl] into a phosphinebased hyper-cross-linked polymer, is proven to be an efficient and general heterogeneous catalyst for the regioselective hydration of a series of alkynes to ketones. Furthermore, the synthesized catalyst is recycled six times without an obvious decrease in the catalytic activity.

引用

页码：7408 / 7416

页数：9

共 64 条

[1] Novel Sulfonated N-Heterocyclic Carbene Gold(I) Complexes: Homogeneous Gold Catalysis for the Hydration of Terminal Alkynes in Aqueous Media [J].

Almassy, Ambroz ;

Nagy, Csilla E. ;

Benyei, Attila C. ;

Joo, Ferenc .

ORGANOMETALLICS, 2010, 29 (11) :2484-2490

[2] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[3] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[4] Gold in Total Synthesis: Alkynes as Carbonyl Surrogates [J].

Brenzovich, William E., Jr. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :8933-8935

[5] HOMOGENEOUSLY CATALYZED HYDRATION OF ACETYLENES BY MERCURIC PERCHLORATE-PERCHLORIC ACID - EVIDENCE FOR A BIS-(ACETYLENE)-MERCURIC ION COMPLEX AS AN INTERMEDIATE [J].

BUDDE, WL ;

DESSY, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (24) :3964-&

[6] 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

[7] Synthesis and Toxicopharmacological Evaluation of m-Hydroxymexiletine, the First Metabolite of Mexiletine More Potent Than the Parent Compound on Voltage-Gated Sodium Channels [J].

Catalano, Alessia ;

Desaphy, Jean-Francois ;

Lentini, Giovanni ;

Carocci, Alessia ;

Di Mola, Antonia ;

Bruno, Claudio ;

Carbonara, Roberta ;

De Palma, Annalisa ;

Budriesi, Roberta ;

Ghelardini, Carla ;

Perrone, Maria Grazia ;

Colabufo, Nicola Antonio ;

Camerino, Diana Conte ;

Franchini, Carlo .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (03) :1418-1422

[8] Trends and challenges for microporous polymers [J].

Chaoui, Nicolas ;

Trunk, Matthias ;

Dawson, Robert ;

Schmidt, Johannes ;

Thomas, Arne .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (11) :3302-3321

[9] A recyclable covalent triazine framework-supported iridium(iii) terpyridine complex for the acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to form quinolines [J].

Chen, Xiaozhong ;

Ai, Yao ;

Liu, Deyun ;

Liu, Peng ;

Xu, Xiangchao ;

Yang, Jiazhi ;

Li, Feng .

MATERIALS CHEMISTRY FRONTIERS, 2022, 6 (09) :1228-1235

[10] Cp*Ir complex bearing a flexible bridging and functional 2,2′- methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol [J].

Chen, Xiaozhong ;

Ai, Yao ;

Liu, Peng ;

Yang, Chenchen ;

Yang, Jiazhi ;

Li, Feng .

JOURNAL OF CATALYSIS, 2021, 402 (402) :325-334

← 1 2 3 4 5 6 7 →