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Borax As An Efficient Metal‐Free Catalyst For Hetero‐Michael Reactions In An Aqueous Medium

S. Hussain, S. Bharadwaj, M. K. Chaudhuri, H. Kalita
Published 2007 · Chemistry

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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.
This paper references
10.1139/CJC-77-5-6-624
ORGANIC REACTION IN WATER. PART 2 : MICHAEL ADDITION IN WATER WITHOUT PHASE TRANSFER AGENTS
F. D. Silva (1999)
10.1016/S0040-4020(03)00289-8
Catalysis by an ionic liquid: efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions
B. Ranu (2003)
10.1021/JA01094A025
Relative Nucleophilic Reactivities of Amino Groups and Mercaptide Ions in Addition Reactions with α,β-Unsaturated Compounds1,2
M. Friedman (1965)
10.1021/JO0163243
Sequential one-pot InBr(3)-catalyzed 1,4- then 1,2-nucleophilic addition to enones.
M. Bandini (2002)
10.1016/S0040-4039(02)01824-5
Regioselective Michael addition of thiols to tertiary fumaric amide esters
A. Kamimura (2002)
10.1016/S1367-5931(02)00331-9
Recent developments in dynamic combinatorial chemistry.
Sijbren Otto (2002)
10.1080/00397910500189783
KF/Al2O3-Mediated Michael Addition of Thiols to Electron‐Deficient Olefins
F. M. Moghaddam (2005)
10.1002/ANIE.199400151
Chemistry and Biology of Taxol
K. C. Nicolaou (1994)
10.1055/S-2005-870010
RuCl3 in Poly(ethylene glycol): A Highly Efficient and Recyclable Catalyst for the Conjugate Addition of Nitrogen and Sulfur Nucleophiles
Huaxing Zhang (2005)
10.1016/S0040-4039(97)01494-9
ZEOLITE MEDIATED MICHAEL ADDITION OF 1,3-DICARBONYL COMPOUNDS AND THIOLS
R. Sreekumar (1997)
10.1016/J.TETLET.2005.09.082
A simple and green procedure for the conjugate addition of thiols to conjugated alkenes employing polyethylene glycol (PEG) as an efficient recyclable medium
A. Kamal (2005)
10.1002/ADSC.200404361
Cu(acac)2 Immobilized in Ionic Liquids: A Recoverable and Reusable Catalytic System for Aza‐Michael Reactions
M. Kantam (2005)
10.1021/JO01056A038
Base-Catalyzed Addition of Thiols to α,β-Unsaturated Anhydrides
F. B. Zienty (1962)
10.1002/ADSC.200404348
Micellar Solution of Sodium Dodecyl Sulfate (SDS) Catalyzes Facile Michael Addition of Amines and Thiols to α,β-Unsaturated Ketones in Water under Neutral Conditions
H. Firouzabadi (2005)
10.1016/S0304-4165(02)00307-0
Chemical biology of dynamic combinatorial libraries.
O. Ramström (2002)
10.1080/17415990500276279
Solid lithium perchlorate-mediated conjugate addition of thiols and indoles to α,β-unsaturated carbonyl compounds
F. Rajabi (2005)
10.1016/S0040-4039(02)02146-9
A natural phosphate and doped-catalyzed Michael addition of mercaptans to α,β-unsaturated carbonyl compounds
Y. Abrouki (2002)
10.1039/CS9962500117
Asymmetric synthesis of ß-amino acids and α-substituted β-amino acids
G. Cardillo (1996)
10.1039/B103334B
Catalytic enantioselective addition of aromatic amines to enones: synthesis of optically active β-amino acid derivatives
Wei Zhuang (2001)
10.1016/S0040-4039(03)01089-X
Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3
M. M. Alam (2003)
10.1002/EJOC.200600006
Perchloric Acid Impregnated on Silica Gel (HClO4/SiO2): A Versatile Catalyst for Michael Addition of Thiols to the Electron-Deficient Alkenes
A. Khan (2006)
10.1016/S0040-4039(00)78552-2
Phosphate naturel et phosphate trisodique : nouveaux catalyseurs solides de la condensation de Knoevenagel en Milieu Hétérogène
S. Sebti (1994)
10.1016/J.TETLET.2005.03.112
Highly efficient KF/Al2O3-catalyzed versatile hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles to α,β-ethylenic compounds
L. Yang (2005)
10.1016/S1359-6446(02)00006-5
Dynamic combinatorial chemistry.
Sijbren Otto (2002)
10.1002/1615-9861(200212)2:12<1672::AID-PROT1672>3.0.CO;2-#
In situ alkylation with acrylamide for identification of cysteinyl residues in proteins during one‐ and two‐dimensional sodium dodecyl sulphate‐polyacrylamide gel electrophoresis
R. Mineki (2002)
10.1002/ANIE.199504551
Enantioselective Synthesis of β‐Amino Acids: TMS‐SAMP as a Chiral Ammonia Equivalent for the Aza Analogous Michael Addition to α,β‐Unsaturated Esters
D. Enders (1995)
10.1016/S0040-4039(00)60361-1
Synthesis in dry media coupled with microwave irradiation: Application to the preparation of β-aminoesters and β-lactams via silyl ketene acetals and aldimines.
F. Texier-Boullet (1993)
10.1021/JO00027A004
Carbonyl-protected .beta.-lithio aldehydes and ketones via reductive lithiation. A general preparative method for remarkably versatile homoenolate equivalents
J. P. Cherkauskas (1992)
10.1016/J.TET.2004.03.052
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
B. Ranu (2004)
10.1039/B414300K
Reversible Michael addition of thiols as a new tool for dynamic combinatorial chemistry.
B. Shi (2005)
10.1039/B411736K
Study of the Michael addition of beta-cyclodextrin-thiol complexes to conjugated alkenes in water.
N. S. Krishnaveni (2005)
10.1055/S-2004-837212
H3PW12O40 as a Useful Recyclable Heterogeneous Catalyst for the Facile and Highly Efficient Michael Addition Reaction of Thiols to α,β-Unsaturated Ketones
H. Firouzabadi (2005)
10.1021/JO026550S
Bismuth nitrate-catalyzed versatile Michael reactions.
N. Srivastava (2003)
10.1016/0040-4039(91)85093-K
Surface-mediated solid phase michael reaction: dramatic acceleration on alumina
B. Ranu (1991)
10.1016/J.TETLET.2005.09.167
Boric acid: a novel and safe catalyst for aza-Michael reactions in water
M. K. Chaudhuri (2005)
10.1016/0003-2697(92)90013-W
Alkylation of cysteine with acrylamide for protein sequence analysis.
D. Brune (1992)
10.1016/S0040-4039(03)00323-X
Fluorapatite: efficient catalyst for the Michael addition
M. Zahouily (2003)
10.1021/JO00315A002
Oxidative functionalization of the .beta.-carbon in .alpha.,.beta.-unsaturated systems. Preparation of 3-phenylthio enones, acrylates, and other vinyl derivatives
P. Bakuzis (1981)
10.1016/S0040-4020(01)00911-5
Clay catalyzed chemoselective Michael type addition of aliphatic amines to α,β-ethylenic compounds
N. Shaikh (2001)
10.1021/OM0009987
Transition Metal-Catalyzed Addition of Amines to Acrylic Acid Derivatives. A High-Throughput Method for Evaluating Hydroamination of Primary and Secondary Alkylamines
Motoi Kawatsura and (2001)
10.1016/S0040-4039(00)92366-9
Highly enantioselective and diastereoselective synthesis of β-amino acid esters and β-lactams from achiral esters and imines
E. Corey (1991)
10.1021/JO034335L
Green Protocol for Conjugate Addition of Thiols to α,β-Unsaturated Ketones Using a [Bmim]PF6/H2O System
J. S. Yadav (2003)
10.1016/S0040-4039(00)97754-2
Dual catalysis of the michael reaction
P. Laszlo (1990)
10.1002/1439-7633(20010601)2:6<445::AID-CBIC445>3.0.CO;2-R
The Outstanding Biological Stability of β‐ and γ‐Peptides toward Proteolytic Enzymes: An In Vitro Investigation with Fifteen Peptidases
J. Frackenpohl (2001)
10.1021/JA980397V
A Catalytic Michael Addition of Thiols to α,β-Unsaturated Carbonyl Compounds: Asymmetric Michael Additions and Asymmetric Protonations
Eita Emori (1998)
10.1021/JO048329G
Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3.7H2O/NaI system supported on alumina in solvent-free conditions.
G. Bartoli (2005)
10.1055/S-2004-834836
Synthesis of β-amino esters via aza-michael addition of amines to alkenes promoted on silica: A useful and recyclable surface
B. Basu (2004)
10.1021/JA00539A040
A stereocontrolled synthesis of (+)-thienamycin
T. Salzmann (1980)
10.1016/S0040-4039(02)01846-4
Na2CaP2O7, a new catalyst for Michael addition
M. Zahouily (2002)



This paper is referenced by
10.1080/00304948.2013.834788
An Expedient Synthesis of β-Acetamido- and β-Benzamidocarbonyl Compounds via KAl(SO4)2·12H2O-catalyzed Three-component Coupling Reaction
Aniruddha Molla (2013)
10.1007/S10562-009-0157-Y
Phosphate Impregnated Titania: An Efficient Reusable Heterogeneous Catalyst for Aza-Michael Reactions Under Solvent-Free Condition
Jayashree Nath (2009)
Manganese (II) Chloride-Catalyzed Conjugated Addition of Amines toElectron Deficient Alkenes in Methanol-Water Medium
A. Roy (2010)
10.1080/17518253.2014.925144
A simple, economical, and environmentally benign protocol for the synthesis of 2-amino-3,5-dicarbonitrile-6-sulfanylpyridines at ambient temperature
U. V. Desai (2014)
10.1246/CL.2007.1244
Diastereoselective Cyanomethylation of Chiral N-(tert-Butylsulfinyl)imines Promoted by Lewis Bases
T. Mukaiyama (2007)
10.1039/C7RA08956B
Thio-Michael addition of α,β-unsaturated amides catalyzed by Nmm-based ionic liquids
Y. Liu (2017)
10.1134/S1070428010040019
Poly(N-vinylimidazole) as an efficient and recyclable catalyst of the aza-Michael reaction in water
I. Beletskaya (2010)
10.1021/co5001713
Cooperative catalysis with block copolymer micelles: a combinatorial approach.
K. Bukhryakov (2015)
10.1016/J.TETLET.2015.05.066
Synthesis and applications of 4-substituted 1-(4-iodophenyl)pyrrolidine-2,5-diones
B. Ali (2015)
10.1039/C4GC01402B
Chitosan: an efficient recyclable catalyst for transamidation of carboxamides with amines under neat conditions
Sadu Nageswara Rao (2014)
10.1016/J.FOODRES.2010.04.033
Stability of acrylamide in model systems and its reactivity with selected nucleophiles
An Adams (2010)
10.1016/J.CCLET.2014.11.018
DABCO-based ionic liquids: Green and efficient catalysts with a dual catalytic role for aza-Michael addition
Hailiang Hou (2015)
10.1016/J.TETLET.2007.03.163
Bromodimethylsulfonium bromide mediated Michael addition of amines to electron deficient alkenes
A. Khan (2007)
10.1039/c5nr08258g
Multifunctional clickable and protein-repellent magnetic silica nanoparticles.
D. Estupiñán (2016)
10.1016/J.TETLET.2009.06.014
Novel synthesis of 3-aminopropionitriles by ring opening of 2-oxazolidinones with cyanide ion
Tsuyoshi Taniguchi (2009)
10.1016/J.TETLET.2008.04.144
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
Gaurav Sharma (2008)
10.1016/J.TET.2009.07.052
Recent advances in the application of bromodimethylsulfonium bromide (BDMS) in organic synthesis
Lokman H Choudhury (2009)
10.1002/SLCT.201801867
Borax Catalysed Domino Synthesis of Highly Functionalised Spirooxindole and Chromenopyridine Derivatives: X‐Ray Structure, Hirshfeld Surface Analysis and Molecular Docking Studies
Aniruddha Molla (2018)
10.1016/J.TET.2008.04.054
Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds
X. Wang (2008)
10.1016/j.chroma.2018.05.021
2-Naphthalenthiol derivatization followed by dispersive liquid-liquid microextraction as an efficient and sensitive method for determination of acrylamide in bread and biscuit samples using high-performance liquid chromatography.
M. Faraji (2018)
10.1080/10426507.2017.1417298
TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole
H. Firouzabadi (2018)
10.1080/00397910903341163
Borax: An Ecofriendly and Efficient Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones under Solvent-Free Conditions
Jayashree Nath (2010)
10.1021/ACSMACROLETT.5B00336
Toward Self-Healing Hydrogels Using One-Pot Thiol–Ene Click and Borax-Diol Chemistry
Lirong He (2015)
10.1039/C4RA15507F
Development of a microfluidic "click chip" incorporating an immobilized Cu(I) catalyst.
H. Li (2015)
10.1007/s10600-014-0862-7
Sulfur-Containing Derivatives of Mono- and Bicyclic Natural Monoterpenoids
G. Ishmuratov (2014)
10.1002/EJOC.201101726
Soluble Polymer‐Supported Flow Synthesis: A Green Process for the Preparation of Heterocycles
N. Prosa (2012)
10.1002/cctc.201600637
NMR and DFT Insight into the Synergistic Role of Bovine Serum Albumin–Ionic Liquid for Multicomponent Cascade Aldol/Knoevenagel–thia‐Michael/Michael Reactions in One Pot
Yogesh Thopate (2016)
10.1039/C3RA43514H
Multicomponent domino reactions: borax catalyzed synthesis of highly functionalised pyran-annulated heterocycles
Aniruddha Molla (2013)
10.1039/C3RA42503G
Novel atom-economic reaction: comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts
Pengchao Gao (2013)
10.1039/C5NJ00867K
One-pot odorless thia-Michael reaction by copper ferrite nanoparticle-catalyzed reaction of elemental sulfur, aryl halides and electron-deficient alkenes
M. Gholinejad (2015)
10.1039/C4RA03627A
Borax catalyzed domino reactions: synthesis of highly functionalised pyridines, dienes, anilines and dihydropyrano[3,2-c]chromenes
Aniruddha Molla (2014)
10.1039/c1ob06346d
Acidic-functionalized ionic liquid as an efficient, green and reusable catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to α,β-unsaturated ketones.
F. Han (2012)
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