Rare Earth Amide-Catalyzed Direct Thioesterification of Aldehydes with Thiols under Mild Conditions

被引：3

作者：

Ismaeel, Nadia ^{[1
]}

Imran, Sajid ^{[1
]}

Zhu, Xuehua ^{[2
]}

Chen, Jue ^{[3
]}

Yuan, Dan ^{[1
]}

Yao, Yingming ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Dushu Lake Campus, Suzhou 215123, Peoples R China

[2] Suzhou Univ Sci & Technol, Sch Chem & Life Sci, Suzhou 215009, Peoples R China

[3] NingboTech Univ, Sch Biol & Chem Engn, Ningbo 315100, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 48期

基金：

中国国家自然科学基金;

关键词：

HOMOGENEOUS CATALYSTS; LANTHANIDE AMIDES; THIOESTERS; HYDROAMINATION; HYDROBORATION; AMIDATION; OXIDATION; COMPLEXES;

D O I：

10.1021/acs.orglett.3c03497

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct thioesterification of aldehydes with thiols catalyzed by readily accessible rare earth/lithium amide RE[N(SiMe3)(2)](3)(mu-Cl)Li(THF)(3) is developed, which enables the preparation of a range of thioesters (31 examples) under room temperature and solvent-free conditions, without using any additive or external oxidant. This method provides a straightforward and atom-efficient approach for the thioester synthesis.

引用

页码：8672 / 8676

页数：5

共 45 条

[1] Direct catalytic conversion of bagasse fibers to furan building blocks in organic and ionic solvents [J].

Abdulkhani, Ali ;

Siahrang, Meraj ;

Zadeh, Zahra Echresh ;

Hedjazi, Sahab ;

Torkameh, Sanaz ;

Faezipour, Mehdi .

BIOMASS CONVERSION AND BIOREFINERY, 2023, 13 (07) :6037-6048

[2] Metal-free thioesterification of α,β-unsaturated aldehydes with thiols [J].

Bolt, Malgorzata ;

Hanek, Kamil ;

Zak, Patrycja .

ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (18) :4846-4853

[3]

Bürgstein MR, 2001, CHEM-EUR J, V7, P3078, DOI 10.1002/1521-3765(20010716)7:14<3078::AID-CHEM3078>3.0.CO

[4]

2-E

[5] The Abiotic Chemistry of Thiolated Acetate Derivatives and the Origin of Life [J].

Chandru, Kuhan ;

Gilbert, Alexis ;

Butch, Christopher ;

Aono, Masashi ;

Cleaves, H. James, II .

SCIENTIFIC REPORTS, 2016, 6

[6] Radii-dependent self-assembly polynuclear lanthanide complexes as catalysts for CO2 transformation into cyclic carbonates [J].

Chen, Changjuan ;

Zhang, Aijiang .

NEW JOURNAL OF CHEMISTRY, 2021, 45 (43) :20155-20163

[7] Tris(cyclopentadienyl)lanthanide Complexes as Catalysts for Hydroboration Reaction toward Aldehydes and Ketones [J].

Chen, Sufang ;

Yan, Dandan ;

Xue, Mingqiang ;

Hong, Yubiao ;

Yao, Yingming ;

Shen, Qi .

ORGANIC LETTERS, 2017, 19 (13) :3382-3385

[8] Poly(3,4-dimethyl-5-vinylthiazolium)/DBU-Catalyzed Thioesterification of Aldehydes with Thiols [J].

Chung, Junyong ;

Seo, Ue Ryung ;

Chun, Supill ;

Chung, Young Keun .

CHEMCATCHEM, 2016, 8 (02) :318-321

[9] Investigation of the inhibitory effects of furfural and hydroxymethylfurfural on the production of Aspergillus niger inulinase and modeling of the process [J].

Gurler, Hilal Nur ;

Coban, Hasan Bugra ;

Turhan, Irfan .

BIOMASS CONVERSION AND BIOREFINERY, 2023, 13 (05) :4291-4303

[10] Tishchenko reactions and Oppenauer oxidation reactions of aldehydes promoted by diisobutylaluminum hydride [J].

Hon, YS ;

Chang, CP ;

Wong, YC .

TETRAHEDRON LETTERS, 2004, 45 (16) :3313-3315

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