Efficient and phosphine-free bidentate N-heterocyclic carbene/ruthenium catalytic systems for the dehydrogenative amidation of alcohols and amines

2019 ◽  
Vol 6 (5) ◽  
pp. 563-570 ◽  
Author(s):  
Xuan-Jun Wu ◽  
Hua-Jing Wang ◽  
Zhao-Qi Yang ◽  
Xiao-Sheng Tang ◽  
Ye Yuan ◽  
...  

An efficient and phosphine-free bidentate NHC/Ru catalytic system was discovered for the dehydrogenative amide synthesis from alcohols and amines.

Processes ◽  
2021 ◽  
Vol 9 (7) ◽  
pp. 1234
Author(s):  
Zhiwei Jiang ◽  
Di Hu ◽  
Zhiyue Zhao ◽  
Zixiao Yi ◽  
Zuo Chen ◽  
...  

Efficient conversion of renewable biomass into value-added chemicals and biofuels is regarded as an alternative route to reduce our high dependence on fossil resources and the associated environmental issues. In this context, biomass-based furfural and levulinic acid (LA) platform chemicals are frequently utilized to synthesize various valuable chemicals and biofuels. In this review, the reaction mechanism and catalytic system developed for the generation of furfural and levulinic acid are summarized and compared. Special efforts are focused on the different catalytic systems for the synthesis of furfural and levulinic acid. The corresponding challenges and outlooks are also observed.


RSC Advances ◽  
2016 ◽  
Vol 6 (69) ◽  
pp. 64749-64755 ◽  
Author(s):  
Masoud Sadeghi ◽  
Javad Safari ◽  
Zohre Zarnegar

An efficient protocol is developed for the synthesis of 2-aminothiazoles from unfunctionalized methylcarbonyl compounds using Fe3O4 nanoparticle-N-halo reagent catalytic systems.


Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2413 ◽  
Author(s):  
Cheng Chen ◽  
Yang Miao ◽  
Kimmy De Winter ◽  
Hua-Jing Wang ◽  
Patrick Demeyere ◽  
...  

Transition-metal-catalyzed amide-bond formation from alcohols and amines is an atom-economic and eco-friendly route. Herein, we identified a highly active in situ N-heterocyclic carbene (NHC)/ruthenium (Ru) catalytic system for this amide synthesis. Various substrates, including sterically hindered ones, could be directly transformed into the corresponding amides with the catalyst loading as low as 0.25 mol.%. In this system, we replaced the p-cymene ligand of the Ru source with a relatively labile cyclooctadiene (cod) ligand so as to more efficiently obtain the corresponding poly-carbene Ru species. Expectedly, the weaker cod ligand could be more easily substituted with multiple mono-NHC ligands. Further high-resolution mass spectrometry (HRMS) analyses revealed that two tetra-carbene complexes were probably generated from the in situ catalytic system.


2005 ◽  
Vol 16 (04) ◽  
pp. 683-705 ◽  
Author(s):  
OSCAR H. IBARRA ◽  
HSU-CHUN YEN ◽  
ZHE DANG

We consider the following definition (different from the standard definition in the literature) of "maximal parallelism" in the application of evolution rules in a P system G: Let R = {r1, …rk} be the set of (distinct) rules in the system. G operates in maximally parallel mode if at each step of the computation, a maximal subset of R is applied, and at most one instance of any rule is used at every step (thus at most k rules are applicable at any step). We refer to this system as a maximally parallel system. We look at the computing power of P systems under three semantics of parallelism. For a positive integer n ≤ k, define: n-Max-Parallel: At each step, nondeterministically select a maximal subset of at most n rules in R to apply (this implies that no larger subset is applicable). ≤ n-Parallel: At each step, nondeterministically select any subset of at most n rules in R to apply. n-Parallel: At each step, nondeterministically select any subset of exactly n rules in R to apply. In all three cases, if any rule in the subset selected is not applicable, then the whole subset is not applicable. When n = 1, the three semantics reduce to the Sequential mode. We focus on two popular models of P systems: multi-membrane catalytic systems and communicating P systems. We show that for these systems, n-Max-Parallel mode is strictly more powerful than any of the following three modes: Sequential, ≤ n-Parallel, or n-Parallel. For example, it follows from the result in [9] that a maximally parallel communicating P system is universal for n = 2. However, under the three limited modes of parallelism, the system is equivalent to a vector addition system, which is known to only define a recursive set. These generalize and refine the results for the case of 1-membrane systems recently reported in [3]. Some of the present results are rather surprising. For example, we show that a Sequential 1-membrane communicating P system can only generate a semilinear set, whereas with k membranes, it is equivalent to a vector addition system for any k ≥ 2 (thus the hierarchy collapses at 2 membranes - a rare collapsing result for nonuniversal P systems). We also give another proof (using vector addition systems) of the known result [8] that a 1-membrane catalytic system with only 3 catalysts and (non-prioritized) catalytic rules operating under 3-Max-Parallel mode can simulate any 2-counter machine M. Unlike in [8], our catalytic system needs only a fixed number of noncatalysts, independent of M. A simple cooperative system (SCO) is a P system where the only rules allowed are of the form a → v or of the form aa → v, where a is a symbol and v is a (possibly null) string of symbols not containing a. We show that a 9-Max-Parallel 1-membrane SCO is universal.


RSC Advances ◽  
2016 ◽  
Vol 6 (69) ◽  
pp. 64338-64343 ◽  
Author(s):  
Zhimin Xue ◽  
Bobo Cao ◽  
Wancheng Zhao ◽  
Jinfang Wang ◽  
Tingting Yu ◽  
...  

Heterogeneous Nb-containing catalyst/N,N-dimethylacetamide–salt mixtures could be used as an efficient catalytic system for the dehydration of fructose to produce 5-hydroxymethylfurfural.


2021 ◽  
Vol 9 ◽  
Author(s):  
Kaijin Lin ◽  
Ang Shi ◽  
Chunhong Shi ◽  
Jinbiao Lin ◽  
Honggui Lin

Amine acid transformation is an important chemical process in biological systems. As a well-developed and acknowledged tool, chiral aldehyde catalysis provides good catalytic activation and stereoselective control abilities in the asymmetric reaction of N-unprotected amino acid esters and amino acid esters analogs, in which the key to success is the design of the catalysts derived from chiral BINOL aldehyde, which is based on the face control of enolate intermediates. In this review, one of the co-catalytic systems that combined with a transition metal to form a multiplex catalytic system and the well-established multiplex stereocenters of chiral aldehyde catalysis have been reviewed. Finally, a novel organocatalysis is prospected.


Author(s):  
Cheng Chen ◽  
Yang Miao ◽  
Kimmy De Winter ◽  
Hua-Jing Wang ◽  
Patrick Demeyere ◽  
...  

Transition-metal-catalyzed amide bond formation from alcohols and amines is an atom-economic and eco-friendly route. Herein, we identified a highly active in situ N-heterocyclic carbene (NHC)/ruthenium (Ru) catalytic system for this amide synthesis. Various substrates, including sterically hindered ones, could be directly transformed into the corresponding amides with the catalyst loading as low as 0.25 mol%. In this system, we replaced the p-cymene ligand of the Ru source with a relatively labile cyclooctadiene (cod) ligand so as to more efficiently obtain the corresponding poly-carbene Ru species. Expectedly, the weaker cod ligand could be more easily substituted with multiple mono-NHC ligands. Further HR-MS analyses revealed that two tetra-carbene complexes were probably generated from the in situ catalytic system.


2017 ◽  
Vol 13 ◽  
pp. 1524-1532 ◽  
Author(s):  
Alexei Nikolaevich Kiselev ◽  
Olga Konstantinovna Grigorova ◽  
Alexei Dmitrievich Averin ◽  
Sergei Aleksandrovich Syrbu ◽  
Oskar Iosifovich Koifman ◽  
...  

The arylation of mono-, di- and tetra-meso-bromophenyl-substituted porphyrins with the heteroarenes containing “acidic” C–H bonds, such as benzoxazole, benzothiazole and N-methylimidazole was studied in the presence of three alternative catalytic systems: Pd(dba)2/DavePhos/Cs2CO3, Pd(PPh3)4/PivOH/K2CO3 and Pd(OAc)2/Cu(OAc)2/PPh3/K2CO3. The first catalytic system was found to be successful in the reaction with benzoxazole, the second one was less efficient for our purpose, while the third system proved to be most versatile and afforded corresponding mono-, di-, tri- and even tetraarylated derivatives of porphyrins.


2020 ◽  
Vol 18 (1) ◽  
pp. 165-174 ◽  
Author(s):  
Abdelaziz Nait Ajjou ◽  
Ateeq Rahman

AbstractDifferent benzylic compounds were efficiently oxidized to the corresponding ketones with aqueous 70% tert-butyl hydroperoxide (TBHP) and the catalytic system composed of CuCl2.2H2O and 2,2’-biquinoline-4,4’-dicarboxylic acid dipotassium salt (BQC). The catalytic system CuCl2/BQC/TBHP allows obtaining high yields at room temperature under organic solvent-free conditions. The interest of this system lies in its cost effectiveness and its benign nature towards the environment. Benzylic tertbutylperoxy ethers and benzylic alcohols were observed and suggested as the reaction intermediates. Analysis of organic products by atomic absorption did not show any contamination with copper metal. In terms of efficiency, CuCl2/BQC system is comparable or superior to the most of the catalytic systems described in the literature and which are based on toxic organic solvent.


2018 ◽  
Vol 762 ◽  
pp. 158-162 ◽  
Author(s):  
Elina Sile ◽  
Valdis Kampars ◽  
Zane Sustere

Two catalytic systems (CH3OK/CH3OH and CH3OK/tert-BuOH) were tested to estimate competitive interesterification-transesterification processes of rapeseed oil with methyl acetate. Catalyst completely dissolves in methanol, while in tert-butanol suspension was obtained. With CH3OK/CH3OH catalytic system high FAME content was obtained (86 wt%), but triacetin content was negligible and without FAME mostly transesterification products of oil and triacetin were observed (up to 94 wt% of all products). When CH3OK/tert-BuOH catalytic system was used, only interesterification of oil proceeded, nevertheless the composition of product complicated the interesterification of triacetin with tert-butanol.


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