Synthesis of Diarylethynes from Aryldiazonium Salts by Using Calcium Carbide as an Alkyne Source in a Deep Eutectic Solvent

被引：27

作者：

Ma, Xiaolong ^{[1
]}

Li, Zheng ^{[1
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China

来源：

SYNLETT | 2021年 / 32卷 / 06期

基金：

中国国家自然科学基金;

关键词：

calcium carbide; aryldiazonium salts; deep eutectic solvents; diarylethynes; alkynes; ONE-POT SYNTHESIS; SONOGASHIRA REACTION; COUPLING REACTION; ACETYLENE SOURCE; DIARYLACETYLENES; DERIVATIVES; FLUORIDE; FACILE; CYCLOADDITION; ETHYNYLATION;

D O I：

10.1055/s-0040-1706638

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of diarylethynes from aryldiazonium salts by using calcium carbide as an alkyne source at room temperature in a deep eutectic solvent is described. The salient features of this protocol are an inexpensive and easy-to-handle alkyne source, a nonvolatile and recyclable solvent, mild conditions, and a simple workup procedure.

引用

页码：631 / 635

页数：5

共 64 条

[31] Ni-Catalyzed Dimerization and Arylation of Diarylacetylenes with Arylboronic Acids [J].

Liu, Yang ;

Zhang, Guoying ;

Huang, Hanmin .

ORGANIC LETTERS, 2017, 19 (24) :6674-6677

[32] Palladium-Catalyzed One-Pot Four-Component Synthesis of β-Cyano-α,β-unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source [J].

Lu, Hao ;

Li, Zheng .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (19) :4474-4482

[33] Phase-Vanishing Method with Acetylene Evolution and Its Utilization in Several Organic Syntheses [J].

Matake, Ryosuke ;

Niwa, Yuki ;

Matsubara, Hiroshi .

ORGANIC LETTERS, 2015, 17 (10) :2354-2357

[34] Pd-catalyzed oxidation of alkynes [J].

Muzart, Jacques .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 338 (1-2) :7-17

[35] Sequential and domino Sonogashira coupling:: Efficient tools for the synthesis of diarylalkynes [J].

Nagy, A ;

Novák, Z ;

Kotschy, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (20) :4453-4461

[36] Recent Advances in the Application of Heterogeneous Nanocaalysts for Sonogashira Coupling Reactions [J].

Nasrollahzadeh, Mahmoud ;

Atarod, Monireh ;

Alizadeh, Mohammad ;

Hatamifard, Arezo ;

Sajadi, S. Mohammad .

CURRENT ORGANIC CHEMISTRY, 2017, 21 (08) :708-749

[37] Gold and palladium combined for the Sonogashira-type cross-coupling of arenediazonium salts [J].

Panda, Biswajit ;

Sarkar, Tarun K. .

CHEMICAL COMMUNICATIONS, 2010, 46 (18) :3131-3133

[38] Facile Access to Diverse Libraries of Internal Alkynes via Sequential Iododediazoniation/Decarboxylative Sonogashira Reaction in Imidazolium ILs without Ligand or Additive [J].

Prabhala, Pavankumar ;

Savanur, Hemantkumar M. ;

Kalkhambkar, Rajesh G. ;

Laali, Kenneth K. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (10) :2061-2064

[39] An Atom-Economic Approach for Vinylation of Indoles and Phenols Using Calcium Carbide as Acetylene Surrogate [J].

Rattanangkool, Eakkaphon ;

Vilaivan, Tirayut ;

Sukwattanasinitt, Mongkol ;

Wacharasindhu, Sumrit .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (25) :4347-4353

[40] Calcium-Based Sustainable Chemical Technologies for Total Carbon Recycling [J].

Rodygin, Konstantin S. ;

Vikenteva, Yulia A. ;

Ananikov, Valentine P. .

CHEMSUSCHEM, 2019, 12 (08) :1483-1516

← 1 2 3 4 5 6 7 →