Carboxylative cyclization of propargylic alcohols with carbon dioxide: A facile and Green route to α-methylene cyclic carbonates

被引:66
作者
Li, Mingli [1 ]
Abdolmohammadi, Shahrzad [2 ]
Hoseininezhad-Namin, Mir Saleh [3 ,4 ]
Behmagham, Farnaz [5 ]
Vessally, Esmail [6 ]
机构
[1] Jining Univ, Dept Life Sci & Engn, Qufu 273155, Shandong, Peoples R China
[2] Islamic Azad Univ, Dept Chem, East Tehran Branch, POB 18735-138, Tehran, Iran
[3] Tabriz Univ Med Sci, Biotechnol Res Ctr, Tabriz, Iran
[4] Tabriz Univ Med Sci, Students Res Comm, Tabriz, Iran
[5] Islamic Azad Univ, Dept Chem, Miyandoab Branch, Miyandoab, Iran
[6] Payame Noor Univ, Dept Chem, Tehran, Iran
关键词
CO2 propargylic alcohols; alpha-Alkylidene cyclic carbonates; Carboxylative cyclization; Organocatalysts; Ionic liquids; HETEROCYCLIC CARBENE-SILVER; CHEMICAL FIXATION; STRAIGHTFORWARD ROUTE; EFFICIENT SYNTHESIS; IONIC-LIQUID; SUSTAINABLE CONVERSION; SELECTIVE SYNTHESIS; CATALYZED SYNTHESIS; CO2; TRANSFORMATION; ATMOSPHERIC CO2;
D O I
10.1016/j.jcou.2020.01.024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transformation of carbon dioxide (CO2) into value-added organic compounds is a very important and hot research topic in green and sustainable chemistry because this greenhouse gas is a plentiful, nontoxic, nonflammable and renewable Cl feedstock. Among the various CO2 fixation reactions, carboxylative cycloaddition of CO2 into propargylic alcohols represents one of the most beautiful and attractive research topics in the field, since it offers the possibility for the fabrication of synthetically and biologically important five-membered cyclic carbonates from the simple and easily accessible starting materials in one step with 100 % atom economy. This review aims to give a comprehensive overview of the titled CO2-fixation reactions, with particular emphasis on the mechanistic features of the reactions. The metal-catalyzed transformations are covered first. This is followed by ionic liquid and organocatalyzed reactions. Finally, the only reported example for electrochemically catalyzed reactions will be discussed at the end of this review.
引用
收藏
页码:220 / 231
页数:12
相关论文
共 100 条
[1]   A Simple and Efficient Synthesis of 4-Arylacridinediones and 6-Aryldiindeno[1,2-b:2,1-e] pyridinediones using CuI Nanoparticles as Catalyst under Solvent-Free Conditions [J].
Abdolmohammadi, Shahrzad ;
Dahi-Azar, Saman ;
Mohammadnejad, Mahdieh ;
Hosseinian, Akram .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2017, 20 (09) :773-780
[2]   A highly efficient CuI nanoparticles-catalyzed synthesis of tetrahydrochromenediones and dihydropyrano[c]chromenediones under grinding [J].
Abdolmohammadi, Shahrzad ;
Ghiasi, Reza ;
Ahmadzadeh-Vatani, Sam .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2016, 71 (07) :777-782
[3]   Rapid and mild synthesis of quinazolinones and chromeno[d]pyrimidinones using nanocrystalline copper(I) iodide under solvent-free conditions [J].
Abdolmohammadi, Shahrzad ;
Karimpour, Samira .
CHINESE CHEMICAL LETTERS, 2016, 27 (01) :114-118
[4]   Simple and Efficient Route Toward Ambient Preparation of Pyrimido[b]Quinolinetriones Using Copper (I) Iodide Nanoparticles in Aqueous Media [J].
Abdolmohammadi, Shahrzad ;
Aghaei-Meybodi, Zahra .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2015, 18 (09) :911-916
[5]   An operationally simple green procedure for the synthesis of dihydropyrimido[4,5-d]pyrimidinetriones using CuI nanoparticles as a highly efficient catalyst [J].
Abdolmohammadi, Shahrzad ;
Afsharpour, Maryam .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2015, 70 (03) :171-176
[6]   Applications of asymmetric organocatalysis in medicinal chemistry [J].
Aleman, Jose ;
Cabrera, Silvia .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :774-793
[7]  
[Anonymous], TOP CURR CHEM
[8]   Solvent-free incorporation of CO2 into 2-oxazolidinones: a review [J].
Arshadi, Sattar ;
Banaei, Alireza ;
Ebrahimiasl, Saeideh ;
Monfared, Aazam ;
Vessally, Esmail .
RSC ADVANCES, 2019, 9 (34) :19465-19482
[9]   Chemical fixation of CO2 to N-propargylamines: A straightforward route to 2-oxazolidinones [J].
Arshadi, Sattar ;
Vessally, Esmail ;
Sobati, Marjan ;
Hosseinian, Akram ;
Bekhradnia, Ahmedreza .
JOURNAL OF CO2 UTILIZATION, 2017, 19 :120-129
[10]   Sustainable Conversion of Carbon Dioxide: An Integrated Review of Catalysis and Life Cycle Assessment [J].
Artz, Jens ;
Mueller, Thomas E. ;
Thenert, Katharina ;
Kleinekorte, Johanna ;
Meys, Raoul ;
Sternberg, Andre ;
Bardow, Andre ;
Leitner, Walter .
CHEMICAL REVIEWS, 2018, 118 (02) :434-504