- Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds
-
A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective α-sulfenylation/β-thiolation of α,β-unsaturated carbonyl compounds. An aromatic sulfur group could be chemoselectively introduced at α-or β-posit
- Huang, Xi,Li, Juan,Li, Xiang,Wang, Jiayi,Peng, Yanqing,Song, Gonghua
-
p. 26419 - 26424
(2019/09/13)
-
- Fe(OTf)2-Catalyzed Thia-Michael Addition Reaction: A Green Synthetic Approach to β-Thioethers
-
A convenient Fe(OTf)2-catalyzed Michael addition reaction of thiols to α,β-unsaturated carbonyl compounds was developed. The use of a simple procedure (EtOH, room temperature, air atmosphere) allowed to set up effective green catalytic conditions for C–S bond formation. The scope of the reaction was demonstrated using various substituted thiols and original Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 99 %). Also, the derivatization into the one-pot thia-Michael addition/oxidation reaction of 3-[3-(phenylthio)butanoyl]oxazolidin-2-one using H2O2 has proven to be efficient.
- Lauzon, Samuel,Li, Mao,Keipour, Hoda,Ollevier, Thierry
-
supporting information
p. 4536 - 4540
(2018/09/06)
-
- Desulfurative Chlorination of Alkyl Phenyl Sulfides
-
The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.
- Canestrari, Daniele,Lancianesi, Stefano,Badiola, Eider,Strinna, Chiara,Ibrahim, Hasim,Adamo, Mauro F. A.
-
supporting information
p. 918 - 921
(2017/02/26)
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- On-water magnetic NiFe2O4 nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes
-
Here, we have demonstrated the Michael addition of active methylene compounds, aromatic/aliphatic amines, thiols and alcohols to conjugated alkenes using magnetic nano-NiFe2O4 as reusable catalyst in water. Nano-NiFe2O4 efficiently catalyzed the formation of C-C and C-X (X = N, S, O etc.) bond through 1,4-addition reactions.
- Payra, Soumen,Saha, Arijit,Banerjee, Subhash
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p. 95951 - 95956
(2016/10/25)
-
- Sonochemical synthesis of lithium fluoride nano cubic as an active and simple catalyst for thia-Michael addition process: Synthesis and structural characterization of β-aryl-β-mercapto ketones
-
LiF nano cubic, with an average particle size of 21.6 nm, was synthesized sonochemically, using tetrabutylammonium fluoride as the fluoride source and characterized by SEM-EDX and XRD. This was applied, as a heterogeneous nano-catalyst, to synthesize some
- Shobeiri, Zohreh,Pourayoubi, Mehrdad,Neas, Marek,Divjakovic, Vladimir,Babiak, Michal
-
p. 245 - 255
(2015/02/19)
-
- Novel and versatile methodology for synthesis of β-aryl-β- mercapto ketone derivatives as potential urease inhibitors
-
The objective was to obtain new scaffold of compounds possessing anti-urease activity. For this new and simple method for the synthesis of β-aryl-β-mercapto ketone derivatives based on Michael addition of thiophenol to chalcones in an ionic liquid as a so
- Ahari-Mostafavi, Mohammad Mahdi,Sharifi, Ali,Mirzaei, Mojtaba,Amanlou, Massoud
-
p. 1113 - 1119
(2014/08/05)
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- Hybrid material from Zn[aminoacid]2 applied in the thio-Michael synthesis
-
Recently, methodologies that are in accordance with green chemistry principles have been garnering increasing attention. One of the most applied methods in this field is heterogeneous catalysis. In this context, many catalysts have been developed, and the
- Darbem, Mariana P.,Oliveira, Aline R.,Winck, Cristiane R.,Rinaldi, Andrelson W.,Domingues, Nelson Luís C.
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p. 5179 - 5181
(2015/01/08)
-
- Synthesis of β-Aryl-β-sulfanyl ketones by a sequential one-pot reaction using kf/al2o3 in glycerol
-
The title compounds were synthesized by a sequential one-pot reaction of aryl aldehydes, aryl-methyl ketones, and thiols promoted by KF/Al2O3. This methodology affords a large number of β-aryl-β-sulfanyl ketone derivatives from aliphatic and aromatic thiols in good yields and is also applicable for solid substrates. Taylor and Francis Group, LLC.
- Perin, Gelson,Mesquita, Katiucia,Calheiro, Tainara P.,Silva, Marcio S.,Lenardao, Eder J.,Alves, Diego,Jacob, Raquel G.
-
-
- Bifunctional acid-base ionic liquid for the one-pot synthesis of fine chemicals: Thioethers, 2H-chromenes and 2H-quinoline derivatives
-
A bifunctional organocatalyst with ionic liquid properties and with an optimized distance between the acid and basic sites efficiently activates electron deficient olefins for 1,4 conjugated addition, which can be incorporated in different one-pot transformations for the preparation of cyclic and acyclic compounds of biological and synthetic interest. More specifically, the catalyst can be successfully applied for different carbon-carbon (CC) and carbon-heteroatom (C-N, C-O, C-S) bond forming reactions integrated in a cascade sequence. The activity of the organocatalyst has been compared with that of structurally related monofunctional and bifunctional catalysts. The most attractive features of this procedure are the high atom economy and the use of inexpensive starting materials as well as the use of an environmentally friendly catalyst that can be easily recovered due to its ionic liquid properties.
- Climent, Maria J.,Iborra, Sara,Sabater, Maria J.,Vidal, Juan D.
-
-
- N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts
-
N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is, NHC·CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.
- Hans, Morgan,Delaude, Lionel,Rodriguez, Jean,Coquerel, Yoann
-
p. 2758 - 2764
(2014/04/17)
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- Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones
-
Two series of chalcone based sulfone and bisulfone derivatives were synthesized using chalcone, thiophenol and sodium metal at room temperature, followed by oxidation of chalcone sulfides with m-CPBA at 0 °C in a novel method. Both sulfones and bisulfones
- Konduru, Naveen Kumar,Dey, Sunita,Sajid, Mohammad,Owais, Mohammad,Ahmed, Naseem
-
-
- Heterobimetallic Pd-Sn catalysis: Michael addition reaction with C-, N-, O-, and S-nucleophiles and in situ diagnostics
-
An efficient Michael addition reaction of differently substituted enones with carbon, sulfur, oxygen, and nitrogen nucleophiles has been achieved by a new heterobimetallic "Pd-Sn" catalyst system. The nature of the catalytically relevant species and their
- Das, Debjit,Pratihar, Sanjay,Roy, Sujit
-
p. 2430 - 2442
(2013/04/23)
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- Two expedient 'one-pot' methods for synthesis of β-aryl-β- mercaptoketones over anhydrous potassium carbonate or amberlyst-15 catalyst
-
Two expedient one-pot methods have been developed for synthesis of β-aryl-β-mercaptoketones using acetophenones, benzaldehydes and thiols as starting materials. The methods involve microwave irradiation (5min) of 1:1 mixtures of acetophenones and benzaldehydes over neutral alumina supported anhydrous potassium carbonate or amberlyst-15 in the first step, and that is followed by addition of thiol to the resulting material and keeping at room temperature for 1.5 h. Indian Academy of Sciences.
- Guha, Chayan,Mondal, Rina,Pal, Rammohan,Mallik, Asok K.
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p. 1463 - 1470
(2014/04/03)
-
- A facile and highly diastereoselective synthesis of cis-2,4- diarylthiochromans
-
A simple methodology has been developed for diastereoselective synthesis of cis-2,4-diarylthiochromans in three steps starting from chalcones. The methodology involves reduction of the conjugate addition product of thiophenol to chalcones followed by Ambe
- Guha, Chayan,Pal, Rammohan,Mallik, Asok K.
-
p. 85 - 94,10
(2020/09/02)
-
- An efficient tandem aldol condensation-thia-Michael addition process
-
An efficient synthesis of β-aryl-β-mercapto ketones is achieved via a tandem aldol condensation-thia-Michael addition process using an aqueous medium and diethylamine. Addition of different thiols to α,β- unsaturated ketones, formed in situ from the condensation of acetophenone derivatives with aldehydes, led to a rapid and high yielding synthesis of the products under very mild conditions using no expensive additive or catalyst. Products which precipitated spontaneously in the reaction mixtures were separated by simple filtration and purified by recrystallization.
- Abaee, M. Saeed,Cheraghi, Somayeh,Navidipoor, Somayeh,Mojtahedi, Mohammad M.,Forghani, Soodabeh
-
experimental part
p. 4405 - 4408
(2012/09/25)
-
- Chiral-Sc catalyzed asymmetric Michael addition/protonation of thiols with enones in water
-
Asymmetric Michael reactions and enantioselective protonations between enones and thiols were catalyzed by a Sc(OTf)3-chiral 2,2′-bipyridine complex in water. The remarkable governing of the enantioselectivity for simple introduction of protons despite their abnormally high mobility in water may provide us with new synthetic opportunities as well as significant chemical advances.
- Kitanosono, Taku,Sakai, Masaru,Ueno, Masaharu,Kobayashi, Shu
-
experimental part
p. 7134 - 7147
(2012/10/08)
-
- Ionic liquid/PPh3 promoted cleavage of diphenyl disulfide and diselenide: A straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides
-
A metal-free cleavage of diphenyl disulfide and diphenyl diselenide has been achieved using ionic liquid/triphenyl phosphine (PPh3) and a convenient protocol for the one-pot synthesis of unsymmetrical sulfides and selenides by condensing 'in situ' generated thiolate or selenate anion with alkyl halides has been developed. In addition, 1,4-conjugate addition of the generated thiolate anions to activated alkenes has also been demonstrated. The ionic liquid, 1-methyl-3-pentyl imidazolium bromide, [pmIm]Br plays a crucial role in promoting the course of the reactions and shows superior activity and selectivity compared to other solvents. The [pmIm]Br has been reused for at least five times without appreciable loss of activity.
- Banerjee, Subhash,Adak, Laksmikanta,Ranu, Brindaban C.
-
supporting information; experimental part
p. 2149 - 2152
(2012/05/05)
-
- Stereoselective thio-Michael addition to chalcones in water catalyzed by bovine serum albumin
-
A biomimetic, inexpensive, and simple method for the stereoselective thio-Michael addition of thiols to chalcones has been developed using bovine serum albumin (BSA) as a catalyst. Optically active products are obtained in high yield and with enantiomeric
- Gaggero, Nicoletta,Albanese, Domenico Carlo Maria,Celentano, Giuseppe,Banfi, Stefano,Aresi, Alice
-
experimental part
p. 1231 - 1233
(2011/10/19)
-
- Design and synthesis of 1,3-biarylsulfanyl derivatives as new anti-breast cancer agents
-
A new series of 1,3-biarylsulfanyl derivatives (homodibenzyl core motif) have been designed and synthesized as new estrogen receptor ligands by chopping benzothiophene core of raloxifene to engender seco-raloxifene scaffold. All the synthesized compounds were screened for anti-proliferative, anti-osteoporotic, and anti-implantation activity. Compounds (35, 36) having basic amino anti-estrogenic side chain were exhibiting potential anti-proliferative activity in MCF-7, MDA-MB-231 and ishikawa cell lines. Some of the synthesized compounds having homodibenzyl motif (5, 8, 10) have shown moderate anti-osteoporotic activity.
- Kumar, Atul,Tripathi, Vishwa Deepak,Kumar, Promod,Gupta, Lalit Prakash,Akanksha,Trivedi, Ritu,Bid, Hemant,Nayak,Siddiqui, Jawed A.,Chakravarti, Bandana,Saxena, Ruchi,Dwivedi, Anila,Siddiquee,Siddiqui,Konwar, Rituraj,Chattopadhyay, Naibedya
-
experimental part
p. 5409 - 5419
(2011/10/31)
-
- Squaric acid as an impressive organocatalyst for Michael addition in water
-
A simple, green, and environmentally benign protocol for squaric acid (5 mg) catalyst conjugate addition of aromatic amines and thiols to unsaturated carbonyl compounds in water in good to excellent yields is developed. The advantages of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, green reaction media and efficient recyclability make this organocatalyst suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls under very mild conditions.
- Azizi, Najmadin,Saki, Elham,Edrisi, Mahtab
-
experimental part
p. 973 - 977
(2012/05/20)
-
- Synthesis and application of modified silica sulfuric acid as a solid acid heterogeneous catalyst in Michael addition reactions
-
Figure represented. Modified silica sulfuric acid (MSSA) as a new type of silica sulfuric acid was prepared and effectively used in the conjugate addition of indole, pyrrole, and thiols with Michael acceptors under mild conditions at room temperature. Als
- Zolfigol, Mohammad Ali,Veisi, Hojat,Mohanazadeh, Farajollah,Sedrpoushan, Alireza
-
experimental part
p. 977 - 986
(2011/09/16)
-
- A mild and highly efficient one-pot three-component reaction for carbon-sulfur bond formation catalyzed by potassium tert-butoxide
-
Potassium tert-butoxide has been found to be a highly efficient catalyst for one-pot, three-component reaction of aryl aldehydes, acetophenones, and thiols via Claisen-Schmidt/Michael addition reactions for the synthesis of thia-Michael adducts in high yields. The reactions are best carried out in tert-butyl alcohol at room temperature.
- Movassagh, Barahman,Rakhshani, Amir
-
experimental part
p. 1179 - 1182
(2012/01/05)
-
- Chiral Sc-catalyzed asymmetric Michael reactions of thiols with enones in water
-
Asymmetric Michael reactions of thiols with enones were catalyzed by a Sc(OTf)3-chiral bipyridine complex at room temperature in water without using any organic solvents, to afford the desired sulfides in high yields with high enantioselectivities.
- Ueno, Masaharu,Kitanosono, Taku,Sakai, Masaru,Kobayashi, Sh
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supporting information; scheme or table
p. 3619 - 3621
(2011/06/10)
-
- A bifunctional cinchona alkaloid-squaramide catalyst for the highly enantioselective conjugate addition of thiols to transchalcones
-
A chiral squaramide catalysts-promoted asymmetric sulfa-Michael conjugated addition of thiols to trans-chalcones is presented. Moderate to excellent yields and high enantioselectivities (up to 99% ee) were achieved under mild conditions.
- Dai, Le,Wang, Su-Xi,Chen, Fen-Er
-
supporting information; experimental part
p. 2137 - 2141
(2010/11/05)
-
- Animal bone meal (ABM): A novel natural catalyst for thia-michael addition
-
The preparation and use of Animal Bone Meal (ABM) as natural catalyst is described for C-S bond formation by thia-Michael addition. This new natural heterogeneous method led to β-sulfinyl adducts in very high yields after only a few minutes. Influence of
- Riadi, Yassine,Mamouni, Rachid,Abrouki, Younes,Haddad, Mohammadine El,Saffaj, Nabil,Antri, Said El,Routier, Sylvain,Guillaumet, Gerald,Lazar, Said
-
experimental part
p. 269 - 271
(2011/07/08)
-
- Phosphonium ionic liquid-catalyzed michael addition of mercaptans to,-Unsaturated ketones
-
A clean and efficient Michael addition reaction on chalcones using phosphonium ionic liquid catalyst (PhosIL-Cl) is described. The method provides several advantages, such as simple workup, environmental friendliness, mild conditions, and excellent yields
- Sarda, Swapnil R.,Jadhav, Wamanrao N.,Shete, Amit S.,Dhopte, Kiran B.,Sadawarte, Sachin M.,Gadge, Prashant J.,Pawar, Rajendra P.
-
experimental part
p. 2178 - 2184
(2010/08/07)
-
- Efficient synthesis of vinyl and alkyl sulfides via hydrothiolation of alkynes and electron-deficient olefins using soluble and heterogenized gold complexes catalysts
-
Soluble and heterogenized gold complexes catalyze the hydrothiolation of alkynes and electron-deficient olefins in high yields and with high anti-Markovnikov selectivity. Moreover heterogenized catalysts could be recycled in several successive runs withou
- Corma, Avelino,González-Arellano, Camino,Iglesias, Marta,Sánchez, Félix
-
scheme or table
p. 49 - 54
(2010/08/06)
-
- Improved design of inherently chiral calix[4]arenes as organocatalysts
-
Improvement of the design of inherently chiral calix[4]arenes as organocatalysts was accomplished via the introduction of a diarylmethanol structure. Novel, inherently chiral calix[4]arenes bearing a tertiary amine or a quaternary ammonium moiety, togethe
- Shirakawa, Seiji,Shimizu, Shoichi
-
experimental part
p. 1217 - 1222
(2010/08/08)
-
- Synthesis and resolution of a multifunctional inherently chiral calix[4]arene with an ABCD substitution pattern at the wide rim: The effect of a multifunctional structure in the organocatalyst on enantioselectivity in asymmetric reactions
-
An efficient synthetic route to inherently chiral calix[4]arenes with an ABCD substitution pattern at the wide rim in the cone conformation was developed for the first time. For the synthesis of inherently chiral ABCD-type calix[4]arenes, first 5,11-dibro
- Shirakawa, Seiji,Kimura, Tomohiro,Murata, Shun-Ichi,Shimizu, Shoichi
-
experimental part
p. 1288 - 1296
(2009/06/28)
-
- Fluoroboric acid adsorbed on silica-gel (HBF4-SiO2) as a new, highly efficient and reusable heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds
-
Fluoroboric acid adsorbed on silica-gel (HBF4-SiO2) has been found to be a new and highly efficient heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds under solvent-free conditions. In the case of
- Sharma, Gaurav,Kumar, Raj,Chakraborti, Asit K.
-
p. 4272 - 4275
(2008/09/21)
-
- Multicomponent, solvent-free synthesis of β-aryl-β-mercapto ketones using zirconium chloride as a catalyst
-
Zirconium chloride efficiently catalyzes the one-pot, three-component reaction of an aryl aldehyde, cyclic or acyclic enolizable ketones, and thiols under solvent-free conditions at room temperature to afford the corresponding β-aryl-β-mercaptoketones via aldol-Michael addition reactions. This methodology affords a large number of β-aryl-β-mercapto ketone derivatives in high yields and in short reaction times.
- Kumar, Atul,Akanksha
-
p. 8730 - 8734
(2008/03/30)
-
- Amino acid catalyzed thio-Michael addition reactions
-
Using amino acid as a catalyst, an inexpensive, nontoxic, environmentally friendly, metal-free reaction procedure for C-S bond formation via thio-Michael addition reaction has been developed. The thio-Michael addition products were obtained in excellent yields under mild and neutral conditions. This metal-free catalytic protocol was found to be a good alternative to the existing metal catalyst methodology for the thio-Michael addition reaction.
- Kumar, Atul,Akanksha
-
p. 11086 - 11092
(2008/02/12)
-
- Natural phosphate modified with lithium nitrate: A new efficient catalyst for the construction of carbon-carbon, carbon-sulfur, and carbon-nitrogen bonds
-
The addition of small amounts of lithium nitrate to natural phosphate followed by calcination gives a new catalyst Li/NP (weight ratio LiNO3/NP = 1/15). This material showed catalytic activity in the Michael addition of amines, mercaptans, and active methylene compounds to chalcone derivatives with high yields under mild reaction conditions. Li/NP is used as the catalyst for a facile synthesis of -amino acids, -sulfur acids, and 4 H-chromenes under heterogeneous conditions. The usual, undesirable byproducts from the Michael condensation such as 1,2-addition, bis-addition, and polymerization compounds are not observed with this method. The work-up procedure is simplified by simple filtration with the use of Li/NP.
- Zahouily, Mohamed,Mounir, Bahija,Cherki, Hind,Bahlaouan, Bouchaib,Rayadh, Ahmed,Sebti, Said
-
p. 1203 - 1217
(2008/02/02)
-
- A simple, efficient, and green procedure for the 1,4-addition of thiols to conjugated alkenes and alkynes catalyzed by sodium acetate in aqueous medium
-
A benign and inexpensive salt, sodium acetate, efficiently catalyzes 1,4-addition of thiols to a variety of conjugated alkenes such as ?,?-unsaturated ketones, aldehydes, carboxylic esters, nitriles, nitro compounds, and chalcones in aqueous THF. The reac
- Ranu, Brindaban C.,Mandal, Tanmay
-
p. 223 - 227
(2008/02/10)
-
- Scope and limitations of HClO4-SiO2 as an extremely efficient, inexpensive, and reusable catalyst for chemoselective carbon-sulfur bond formation
-
The scope and limitations of perchloric acid adsorbed on silica gel (HClO4-SiO2) as a highly efficient, inexpensive, and reusable catalyst for chemoselective carbon-sulfur bond formation by conjugate addition of thiols to α,β-unsatur
- Khatik, Gopal L.,Sharma, Gaurav,Kumar, Raj,Chakraborti, Asit K.
-
p. 1200 - 1210
(2007/10/03)
-
- Ceric ammonium nitrate (CAN) as a green and highly efficient promoter for the 1,4-addition of thiols and benzeneselenol to α,β-unsaturated ketones
-
A mild and efficient process for the 1,4-addition of thiols and benzeneselenols to various α,β-unsaturated ketones using a catalytic amount of CAN with excellent product yields is described. This inexpensive, nontoxic, and readily available catalytic ceric(IV) ammonium nitrate system efficiently catalyzes conjugate addition reactions between thiol derivatives and various α,β-unsaturated ketones under solvent-free conditions. A plausible mechanism for the role of CAN, both as a promoter in free radical chain addition reactions as well as a catalyst for the conjugate addition process is proposed.
- Chu, Cheng-Ming,Gao, Shijay,Sastry,Kuo, Chun-Wei,Lu, Chaowei,Liu, Ju-Tsung,Yao, Ching-Fa
-
p. 1863 - 1871
(2007/10/03)
-
- Borax as an efficient metal-free catalyst for hetero-Michael reactions in an aqueous medium
-
Borax, a naturally occurring material, very efficiently catalyzed the conjugate addition of thiols, dithiols and amines to α,β-unsaturated ketones, nitriles, amides, aldehydes and esters in an aqueous medium to afford the corresponding Michael adducts in good yields at room temperature. Recycling of the catalyst and scaling up of the reactions are important attributes of this catalysis. The reactions of thiols and dithiols were relatively more facile than those of the corresponding amines. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Hussain, Sahid,Bharadwaj, Saitanya K.,Chaudhuri, Mihir K.,Kalita, Harjyoti
-
p. 374 - 378
(2007/10/03)
-
- L-proline catalyzed michael additions of thiophenols to α,βunsaturated compounds, particularly α-enones, in the ionic liquid [bmim]PF6
-
L-Proline catalyzed additions of 13 different thiols to 11 different a-enone Michael acceptors in [bmim] PF6 are reported. Reasonable to high yields of the reaction products were isolated in most cases.
- Kotrusz, Peter,Toma, Stefan
-
p. 197 - 205
(2007/10/03)
-
- The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions
-
The 1,4-addition of various thiols to α,β-unsaturated ketones was completed rapidly in the presence of a catalytic amount (2-3 mol %) of anhydrous iron(III) chloride under solvent free conditions and an air atmosphere. Anhydrous iron(III) chloride is more active than that of other ferric salts. With more reactive and/or less steric reagents (1a-c and/or 2a-2c), expeditious conditions (short reaction times at room temperature) could be employed. With less reactive and/or steric reagents (1d-g and/or 2d-e), a slight increase in reaction time was required, but high yields were obtained. The FeCl3 catalyst causes preferential interactions with α,β-unsaturated ketones present in the reaction.
- Chu, Cheng-Ming,Huang, Wan-Ju,Lu, Chaowei,Wu, Pohsi,Liu, Ju-Tsung,Yao, Ching-Fa
-
p. 7375 - 7380
(2007/10/03)
-
- Perchloric acid impregnated on silica gel (HClO4/SiO 2): A versatile catalyst for Michael addition of thiols to the electron-deficient alkenes
-
Perchloric acid adsorbed on silica gel (HClO4X/SiO2) has been found to be a highly efficient and versatile catalyst for the Michael addition of thiols to a wide variety of conjugated alkenes such as α,α-unsaturated ketones, carboxylic esters, nitriles, amides and chalcones in dichloromethane or methanol at room temperature. The reactions are completed within 2-20 min in high yields. Some of the additional advantages are: no aqueous work-up is necessary, and the catalyst is also reusable. Moreover, the solid product can be obtained without chromatographic separation. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Khan, Abu T.,Ghosh, Subrata,Choudhury, Lokman H.
-
p. 2226 - 2231
(2007/10/03)
-
- Michael addition of thiols to α-enones in ionic liquids with and without organocatalysts
-
Seventeen organocatalyts were tested for their ability to catalyst the addition of thiophenols to chalcones in [bmim]PF6. The products were isolated in high yield after a short reaction time, but no stereoselectivity was observed. The reactions
- Meciarova, Maria,Toma, Sefan,Kotrusz, Peter
-
p. 1420 - 1424
(2007/10/03)
-
- Potassium phosphate or silica sulfuric acid catalyzed conjugate addition of thiols to α,β-unsaturated ketones at room temperature under solvent-free conditions
-
Potassium phosphate and silica sulfuric acid have been found to be useful and highly efficient catalysts for conjugate addition of thiols to α,β-unsaturated ketones under solvent-free conditions, at room temperature. Silica sulfuric acid (SSA) was found t
- Pore,Soudagar,Desai,Thopate,Wadagaonkar
-
p. 9325 - 9328
(2007/10/03)
-
- An efficient and improved synthesis of 1,5-diketones: versatile conjugate addition of nucleophiles to α,β-unsaturated enones and alkynones
-
Several 1,5-diketones have been prepared in good to excellent yields by versatile conjugate addition of nucleophiles such as cyclic or acyclic ketones, amines and thiols to α,β-unsaturated enones and alkynones, in the presence of catalytic amounts of 10%
- Shankar, Ravi,Jha, Ashok K.,Singh, Uma Sharan,Hajela
-
p. 3077 - 3079
(2007/10/03)
-
- Ring-closure reactions through intramolecular substitution of thiophenoxide by oxygen and nitrogen nucleophiles: Simple stereospecific synthesis of 4,5-dihydroisoxazoles and 4,5-dihydropyrazoles
-
A new and simple method for the stereospecific synthesis of 3,5-disubstituted-4,5-dihydro-isoxazoles (chiral isoxazolines) from readily available oximes of chiral Michael adducts of thiophenol to chalcones is reported. An analogous reaction with the N-arylhydrazones of the Michael adduct gave nonracemic 1-(aryl)-3,5-diphenyl-4,5-dihydro-1H-pyrazoles (chiral pyrazolines), but these products are configurationally unstable. The key step of the synthesis is the ring-closure reaction, which occurs by a stereospecific intramoleculer nucleophilic substitution of thiophenoxide.
- Zielinska-B?ajet, Mariola,Kowalczyk, Rafa?,Skarzewski, Jacek
-
p. 5235 - 5240
(2007/10/03)
-
- Iodine-catalyzed Michael addition of mercaptans to α,β- unsaturated ketones under solvent-free conditions
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A simple and efficient method for the Michael reaction between various mercaptans and α,β-unsaturated ketones using a catalytic amount of iodine (5 mol %) to generate the 1,4-adduct has been reported. The significant features of the iodine catalyzed Micha
- Chu, Cheng-Ming,Gao, Shijay,Sastry,Yao, Ching-Fa
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p. 4971 - 4974
(2007/10/03)
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- Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for Michael addition of mercaptans to α,β-unsaturated carbonyl compounds
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Copper(II) tetrafluoroborate has been found to be a new and highly efficient catalyst for Michael addition of thiols to α,β-unsaturated carbonyl compounds under solvent-free conditions and in H2O at room temperature. The reactions are very fast
- Garg, Sanjeev K.,Kumar, Raj,Chakraborti, Asit K.
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p. 1721 - 1724
(2007/10/03)
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- Zinc perchlorate hexahydrate catalysed conjugate addition of thiols to α,β-unsaturated ketones
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Zn(II) perchlorate hexahydrate has been found to be a new and efficient catalyst for conjugate addition of thiols to α,β-unsaturated ketones under solvent-free conditions at room temperature. The reaction of aryl, arylalkyl and alkyl thiols with cyclic an
- Garg, Sanjeev K.,Kumar, Raj,Chakraborti, Asit K.
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p. 1370 - 1374
(2007/10/03)
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- TMAF-catalyzed conjugate addition of oxazolidinone and thiols
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TMAF (Me4NF) is a useful catalyst for the conjugate addition of oxazolidinone and thiols to a range of Michael acceptors including esters, ketones, nitroolefins and cinnamaldehyde.
- Ménand, Micka?l,Dalla, Vincent
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- Catalysis by ionic liquid: A simple, green and efficient procedure for the Michael addition of thiols and thiophosphate to conjugated alkenes in ionic liquid, [pmIm]Br
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A room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes Michael addition of thiols and diethyl dithiophosphate to a variety of conjugated alkenes such as α,β- unsaturated carbonyl compounds, carboxylic esters,
- Ranu, Brindaban C.,Dey, Suvendu S.
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p. 4183 - 4188
(2007/10/03)
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- Green protocol for conjugate addition of thiols to α,β -unsaturated ketones using a [Bmim] PF6/H2O system
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α,β-Unsaturated ketones undergo conjugate addition rapidly with thiols in a hydrophobic ionic liquid [bmim] PF6/H2O solvent system (2:1) in the absence of any acid catalyst to afford the corresponding Michael adducts in high to quant
- Yadav,Reddy,Baishya, Gakul
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p. 7098 - 7100
(2007/10/03)
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