Thia-Michael Reaction under Heterogeneous Catalysis
Giovanna Bosica, Roderick Abdilla, Alessio Petrellini
Organics · pp. 86–96 · Published 21 Feb 2023
10.3390/org4010007Abstract
Thia-Michael reactions between aliphatic and aromatic thiols and various Michael acceptors were performed under environmentally-friendly solvent-free conditions using Amberlyst® A21 as a recyclable heterogeneous catalyst to efficiently obtain the corresponding adducts in high yields. Ethyl acrylate was the main acceptor used, although others such as acrylamide, linear, and cyclic enones were also utilized successfully. Bifunctional Michael donor, 3-mercaptopropanoic acid, positively furnished the product, albeit in a lower yield and after leaving the reaction to take place for a longer time. The catalyst was easy and safe to handle and successfully recycled for five consecutive cycles.
References (27)
- 1 Kumar, 2007, Amino acid catalyzed thia-Michael addition reactions [DOI]
- 2 Wadhwa, 2018, Thia-Michael addition: An emerging strategy in organic synthesis [DOI]
- 3 Feng, 2016, Sulphur containing scaffolds in drugs: Synthesis and application in medicinal chemistry [DOI]
- 4 Thiol, 1964, The thermal reversibility of the Michael reaction [DOI]
- 5 Nicponski, 2014, Selectivity reversal during thia-Michael additions using tetrabutylammonium hydroxide: Operationally simple and extremely high turnover [DOI]
- 6 Bandini, 2002, Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [DOI]
- 7 Pore, 2006, Potassium phosphate or silica sulphuric acid catalyzed conjugate addition of thiols to α,β-unsaturated ketones at room temperature under solvent-free conditions [DOI]
- 8 Wadhwa, 2017, A Regioselective multicomponent cascade to access thiosemicarbazone-fused thiazinones: Scope, structure elucidation and gram scale synthesis [DOI]
- 9 Bosica, G., and Abdilla, R. (2016). Aza-Michael Mono-addition Using Acidic Alumina under Solventless Conditions. Molecules, 21. [DOI]
- 10 Bosica, 2022, Aza-Michael Mono- and Bis-Addition of Primary and Secondary Amines Promoted by Silica-Supported Polyphosphoric Acid, PPA/SiO2 [DOI]
- 11 Park, 2022, One-pot sulfa-Michael addition reactions of disulfides using a pyridine-borane complex under blue light irradiation [DOI]
- 12 Xu, 2009, Reduction cleavage of S-S bond by Zn/Cp2TiCl2: Application for the synthesis of β-arylthiocarbonyl compounds [DOI]
- 13 Abbasi, 2020, CuI-catalyzed tandem synthesis of thioethers using aryl halides, electron-deficient alkenes, and sodium iso-propyl xanthogenate [DOI]
- 14 Hans, 2014, N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts [DOI]
- 15 Beletskaya, 2007, Poly(N-vinylimidazole) as efficient and recyclable catalyst for the addition of thiols to Michael acceptors in aqueous medium [DOI]
- 16 Moghaddam, 2005, KF/Al2O3-mediated Michael addition of thiols to electron-deficient olefins [DOI]
- 17 Payra, 2016, On-water magnetic NiFe2O 4 nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes [DOI]
- 18 Civit, 2015, Thioboration of α,β-unsaturated ketones and aldehydes toward the synthesis of β-sulfido carbonyl compounds [DOI]
- 19 Firouzabadi, 2015, Dithiooxamide as an effective sulphur surrogate for odourless high-yielding carbon-sulphur bond formation in wet PEG200 as an eco-friendly, safe, and recoverable solvent [DOI]
- 20 Barbero, 2013, O-Benzenedisulfonimide as a reusable Brønsted acid catalyst for hetero-Michael reactions [DOI]
- 21 Thiyagarajan, 2020, KOtBu-catalyzed Michael addition reactions under mild and solvent-free conditions [DOI]
- 22 Yang, 2018, Nmp-based ionic liquids: Recyclable catalysts for both hetero-Michael addition and Knoevenagel condensation in water [DOI]
- 23 Sigma, A. (2023, February 06). Amberlyst(R) A21 Free Base. Available online: https://www.sigmaaldrich.com/MT/en/product/aldrich/216410.
- 24 Bonfils, 2006, Michael reactions carried out using a bench-top flow system [DOI]
- 25 Bosica, 2018, One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions [DOI]
- 26 Khan, 2006, Perchloric acid impregnated on silica gel: A versatile catalyst for Michael addition of thiols to the electron-deficient alkenes [DOI]
- 27 Zhang, 2005, RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulphur nucleophiles [DOI]
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