19360-96-4Relevant academic research and scientific papers
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
Chu, Cheng-Ming,Gao, Shijay,Sastry,Kuo, Chun-Wei,Lu, Chaowei,Liu, Ju-Tsung,Yao, Ching-Fa
, p. 1863 - 1871 (2007)
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.
The ionic liquid ethyltri-n-butylphosphonium tosylate as solvent for the acid-catalysed hetero-Michael reaction
Karodia, Nazira,Liu, Xihan,Ludley, Petra,Pletsas, Dimitrios,Stevenson, Grace
, p. 11039 - 11043 (2006)
A new and convenient method for the acid-catalysed Michael addition reactions of alcohols, thiols and amines to methyl vinyl ketone has been developed using the ionic liquid ethyltri-n-butylphosphonium tosylate. The reaction conditions are mild and obviat
To Coordinate or not to Coordinate: The Special Role of Chalcogen Ether Functionalities in the Design of Twofold Functionalized Cyclopentadienyl Ligands [Cp,O,Ch (Ch = S, Se)]
Fischer, Malte,Schmidtmann, Marc,Beckhaus, Ruediger
, p. 595 - 604 (2019)
The solvent- and catalyst free synthesis of two β-thio ketones L1a and L1b is reported. L1a, L1b, and a β-seleno ketone L1c were successfully employed as ligand precursors in the synthesis of a novel series of cationic titanium complexes 4a–4c via a well-
Photo-Biocatalytic Cascades for the Synthesis of Volatile Sulfur Compounds and Chemical Building Blocks
Castagnolo, Daniele,Lauder, Kate
, p. 737 - 744 (2020/05/19)
Biocatalysis is a branch of catalysis that exploits enzymes to perform highly stereoselective chemical transformations under mild and sustainable conditions. This Synpact highlights how biocatalysis can be used in the synthesis of chiral 1,3-mercaptoalkan
Photo-biocatalytic One-Pot Cascades for the Enantioselective Synthesis of 1,3-Mercaptoalkanol Volatile Sulfur Compounds
Lauder, Kate,Toscani, Anita,Qi, Yuyin,Lim, Jesmine,Charnock, Simon J.,Korah, Krupa,Castagnolo, Daniele
supporting information, p. 5803 - 5807 (2018/04/19)
The synthesis of enantiomerically pure 1,3-mercaptoalkanol volatile sulfur compounds through a one-pot photo-biocatalytic cascade reaction is described. Two new KRED biocatalysts with opposite enantioselectivity were discovered and proved to be efficient
An atom-economic and odorless thia-Michael addition in a deep eutectic solvent
Azizi, Najmedin,Yadollahy, Zahra,Rahimzadeh-Oskooee, Amin
, p. 1722 - 1725 (2014/03/21)
The first 100% atom-efficient and odorless protocol for carbon-sulfur bond formation in a deep eutectic solvent (DES) as both the reaction medium and catalyst is reported. The biodegradable and inexpensive DES provides an efficient and convenient ionic reaction medium for the thia-Michael addition with in situ generation of S-alkylisothiouronium salts in place of thiols without the urea by-product segment. This protocol offers several advantages including short reaction times, high yields, clean reactions, and inexpensive and commercially available starting materials.
Mild hydrosulfenylation of Olefins under neutral conditions using a defined NHC-ligated iron-sulfur catalyst
Alt, Isabel,Rohse, Philipp,Plietker, Bernd
, p. 3002 - 3005 (2014/01/06)
A defined NHC-Fe-S complex proved to be an efficient catalyst for the selective hydrosulfenylation of α,β-unsaturated ketones or vinylnitriles. A wide range of different aliphatic thiols were transferred in this atom-economic reaction into the correspondi
O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
, p. 758 - 767 (2013/01/15)
The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and ,-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Brnsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Synthesis and application of modified silica sulfuric acid as a solid acid heterogeneous catalyst in Michael addition reactions
Zolfigol, Mohammad Ali,Veisi, Hojat,Mohanazadeh, Farajollah,Sedrpoushan, Alireza
experimental part, p. 977 - 986 (2011/09/16)
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
One-step synthesis of N-acetylcysteine and glutathione derivatives using the Ugi reaction
Zhdanko, Alexander G.,Gulevich, Anton V.,Nenajdenko, Valentine G.
experimental part, p. 4692 - 4702 (2009/10/02)
Fully protected natural and unnatural N-acetylcysteine, dipeptide Cys-Gly, glutathione, and homoglutathione derivatives were synthesized by the Ugi four-component reaction using various benzylthio aldehydes and ketones as carbonyl building blocks. The scope and limitations of the method were investigated. Formation of imidazoline by-products in the Ugi reaction was discussed. 2,2,2-Trifluoroethanol was shown to be a superior reaction media than methanol in some reactions. Also, the 4-methyl-2,6,7-trioxabicyclo[2.2.2]octyl derivative (OBO-ester) of isocyanoacetic acid was shown to be superior to use than ethyl isocyanoacetate as a peptide synthesis precursor in cases when higher reactivity of an isocyanide is required.
