75717-34-9Relevant academic research and scientific papers
Zinc complexes supported by pyridine-: N -oxide ligands: Synthesis, structures and catalytic Michael addition reactions
Chen, Ze-Wen,He, Piao,Liu, Chao,Mo, Xiu-Fang,Tong, Hai-Xia,Xiong, Chang-Feng,Yi, Xiao-Yi
, p. 12365 - 12371 (2020/10/02)
New dipyridylpyrrole N-oxide ligands HL1 and HL2 are designed and synthesized via oxidation of 2-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)pyridine (Hdpp) by using 3-chloroperbenzoic acid (m-CPBA) in CH2Cl2. The treatment of ZnEt2 with two equiv. of HL1 and HL2 af
Four-Component Catalytic Machinery: Reversible Three-State Control of Organocatalysis by Walking Back and Forth on a Track
Mittal, Nikita,?zer, Merve S.,Schmittel, Michael
supporting information, p. 3579 - 3586 (2018/04/06)
A three-component supramolecular walker system is presented where a two-footed ligand (biped) walks back and forth on a tetrahedral 3D track upon the addition and removal of copper(I) ions, respectively. The addition of N-methylpyrrolidine as a catalyst t
Catalytic Three-Component Machinery: Control of Catalytic Activity by Machine Speed
Paul, Indrajit,Goswami, Abir,Mittal, Nikita,Schmittel, Michael
supporting information, p. 354 - 358 (2017/12/29)
Three supramolecular slider-on-deck systems DS1–DS3 were obtained as two-component aggregates from the sliders S1–S3 and deck D with its three zinc porphyrin (ZnPor) binding sites. The binding of the two-footed slider to the deck varies with the donor qua
Networking Nanoswitches for ON/OFF Control of Catalysis
Mittal, Nikita,Pramanik, Susnata,Paul, Indrajit,De, Soumen,Schmittel, Michael
, p. 4270 - 4273 (2017/04/03)
The nanoswitches 1 and 2 are interdependently linked in so-called network states (NetStates). In NetState I, defined by presence of [Cu(1)]+ and 2, the organocatalyst N-methylpyrrolidine catalyzes a conjugate addition. Addition of iron(II) ions as an external chemical trigger to NetState I discharges Cu+ from [Cu(1)]+. The liberated copper(I) ion acts as a second messenger and changes the toggling state at nanoswitch 2. The resulting nanoswitch [Cu(2)]+ captures the catalytically active species from solution and the conjugate addition is turned OFF. Removal of the original trigger reverses the sequence and turns catalysis ON. The ON/OFF catalytic cycle was run three times in situ.
Thioboration of α,β-unsaturated ketones and aldehydes toward the synthesis of β-sulfido carbonyl compounds
Civit, Marc G.,Sanz, Xavier,Vogels, Christopher M.,Webb, Jonathan D.,Geier, Stephen J.,Decken, Andreas,Bo, Carles,Westcott, Stephen A.,Fernández, Elena
supporting information, p. 2148 - 2154 (2015/05/19)
Herein a direct β-sulfido carbonyl compound synthesis by the easy activation of RS-Bpin reagents with α,β-unsaturated ketones and aldehydes is reported. This convenient methodology can be performed at room temperature with no other additives. The key poin
Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex
Yang, Yong,Rioux, Robert M.
, p. 3916 - 3925 (2014/08/05)
A practical, efficient, and low-cost heterogeneous catalyst consisting of a Cu-NHC (N-heterocyclic carbene) complex grafted to SBA-15 silica for the catalytic hydrothiolation of alkynes and electron-deficient alkenes under mild reaction conditions has been developed. The heterogeneous catalyst displays higher activity and stereoselectivity to Z-anti-Markovnikov isomers compared with the homogeneous analog under otherwise identical reaction conditions. The catalytic system is applicable to a broad range of alkynes and thiols and is recyclable without significant loss in catalytic performance. High activity and perfect selectivity to alkyl sulfides formed by the addition of electron-deficient alkenes to various thiols catalyzed by the supported Cu-NHC complex were also realized. This journal is the Partner Organisations 2014.
Selectivity reversal during thia-Michael additions using tetrabutylammonium hydroxide: Operationally simple and extremely high turnover
Nicponski, Daniel R.,Marchi, Jennifer M.
supporting information, p. 1725 - 1730 (2014/07/08)
The use of tetrabutylammonium hydroxide as a novel and exceedingly efficient thia-Michael addition catalyst is herein described. This extremely simple methodology allows for the conjugate addition of a wide variety of mercaptan nucleophiles, and functions remarkably well with a very wide range of both classical and non-classical Michael acceptors. Contradistinctive to current literature reports, the use of this catalyst more efficiently promotes the addition of more basic thiols. This methodology is especially attractive and operationally simple, as it generally proceeds with only 1 mol% catalytic loading and without excess reagent, and the produced products typically require no purification. Georg Thieme Verlag Stuttgart New York.
Asymmetrie ruthenium-catalyzed 1,4-additions of aryl thiols to enones
Badoiu, Andrei,Bernardinelli, Gerald,Besnard, Celine,Peter Kuendig
supporting information; experimental part, p. 193 - 200 (2010/04/25)
Well defined, stable, one-point binding ruthenium complexes 1 and 2 selectively bind and activate α,β-unsaturated carbonyl compounds for cycloaddition reactions. These mild Lewis acids catalyze asymmetric 1,4-addition reactions of aryl thiols to enones wi
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
Sharma, Gaurav,Kumar, Raj,Chakraborti, Asit K.
, p. 4272 - 4275 (2008/09/21)
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
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 (2007/10/03)
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.
