Diels-Alder Cycloaddition Reactions in Sustainable Media

被引：20
作者：
Soares, Maria I. L. [1 ,2 ]
Cardoso, Ana L. [1 ,2 ]
Melo, Teresa M. V. D. Pinho E. [1 ,2 ]
机构：
[1] Univ Coimbra, Coimbra Chem Ctr, Inst Mol Sci, P-3004535 Coimbra, Portugal
[2] Univ Coimbra, Dept Chem, P-3004535 Coimbra, Portugal
来源：
MOLECULES | 2022年 / 27卷 / 04期
关键词：
Diels-Alder reaction; green solvent; bio-based solvent; deep eutectic solvents; water; DEEP EUTECTIC SOLVENTS; CATALYST-FREE SYNTHESIS; ANNULATED THIOPYRANOCOUMARIN DERIVATIVES; SUPERCRITICAL CARBON-DIOXIDE; BIOMASS-DERIVED SOLVENTS; DOMINO-KNOEVENAGEL; ORGANIC-SYNTHESIS; ON-WATER; ONE-POT; DIASTEREOSELECTIVE SYNTHESIS;
D O I：
10.3390/molecules27041304
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Diels-Alder cycloaddition reaction is one of the most powerful strategies for the construction of six-membered carbocyclic and heterocyclic systems, in most cases with high regio- and stereoselectivity. In this review, an insight into the most relevant advances on sustainable Diels-Alder reactions since 2010 is provided. Various environmentally benign solvent systems are discussed, namely bio-based derived solvents (such as glycerol and gluconic acid), polyethylene glycol, deep eutectic solvents, supercritical carbon dioxide, water and water-based aqueous systems. Issues such as method's scope, efficiency, selectivity and reaction mechanism, as well as sustainability, advantages and limitations of these reaction media, are addressed.
引用
收藏
页数：46
相关论文
共 160 条
[31]   L-Proline-Catalysed One-Pot aza-Diels-Alder Reaction in Water: Regioselective Synthesis of Spiro(isoxazolo[5,4-b]pyridine-5,5'-pyrimidine) Derivatives [J].
Dommaraju, Yuvaraj ;
Borthakur, Somadrita ;
Prajapati, Dipak .
SYNLETT, 2018, 29 (09) :1195-1198
[32]   Supercritical fluids as solvents for chemical and materials processing [J].
Eckert, CA ;
Knutson, BL ;
Debenedetti, PG .
NATURE, 1996, 383 (6598) :313-318
[33]   The Green ChemisTREE: 20 years after taking root with the 12 principles [J].
Erythropel, Hanno C. ;
Zimmerman, Julie B. ;
de Winter, Tamara M. ;
Petitjean, Laurene ;
Melnikov, Fjodor ;
Lam, Chun Ho ;
Lounsbury, Amanda W. ;
Mellor, Karolina E. ;
Jankovic, Nina Z. ;
Tu, Qingshi ;
Pincus, Lauren N. ;
Falinski, Mark M. ;
Shi, Wenbo ;
Coish, Philip ;
Plata, Desiree L. ;
Anastas, Paul T. .
GREEN CHEMISTRY, 2018, 20 (09) :1929-1961
[34]   Biodegradable hyaluronic acid hydrogels to control release of dexamethasone through aqueous Diels-Alder chemistry for adipose tissue engineering [J].
Fan, Ming ;
Ma, Ye ;
Zhang, Ziwei ;
Mao, Jiahui ;
Tan, Huaping ;
Hu, Xiaohong .
MATERIALS SCIENCE & ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS, 2015, 56 :311-317
[35]   Dimethyl carbonate: a versatile reagent for a sustainable valorization of renewables [J].
Fiorani, G. ;
Perosa, A. ;
Selva, M. .
GREEN CHEMISTRY, 2018, 20 (02) :288-322
[36]   Catalytic Asymmetric Aza-Diels-Alder Reactions: The Povarov Cycloaddition Reaction [J].
Fochi, Mariafrancesca ;
Caruana, Lorenzo ;
Bernardi, Luca .
SYNTHESIS-STUTTGART, 2014, 46 (02) :135-157
[37]  
Forero JSB, 2015, CURR ORG SYNTH, V12, P102
[38]   Mechanisms of the Knoevenagel hetero Diels-Alder sequence in multicomponent reactions to dihydropyrans: experimental and theoretical investigations into the role of water [J].
Frapper, Gilles ;
Bachmann, Christian ;
Gu, Yanlong ;
De Sousa, Rodolphe Coval ;
Jerome, Francois .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (02) :628-636
[39]   Influence of Non-Covalent Interactions in the Exo- and Regioselectivity of Aza-Diels-Alder Reactions: Experimental and DFT Calculations [J].
Gallardo-Fuentes, Sebastian ;
Lezana, Nicolas ;
Luhr, Susan ;
Galdamez, Antonio ;
Vilches-Herrera, Marcelo .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17) :10825-10831
[40]   Biomass-Derived Solvents for Sustainable Transition Metal-Catalyzed C-H Activation [J].
Gandeepan, Parthasarathy ;
Kaplaneris, Nikolaos ;
Santoro, Stefano ;
Vaccaro, Luigi ;
Ackermann, Lutz .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (09) :8023-8040
12345678910