Active palladium catalyst supported by bulky diimine ligand catalyzed Suzuki-Miyauracoupling reaction in water under phosphane-free and low catalyst loading conditions

2014 ◽  
Vol 28 (4) ◽  
pp. 221-224 ◽  
Author(s):  
Mohammad Gholinejad ◽  
Vahid Karimkhani ◽  
Il Kim
Keyword(s):  
Palladium Catalyst ◽  
Catalyst Loading ◽  
Loading Conditions ◽  
Diimine Ligand ◽  
Low Catalyst Loading ◽  
Reaction In Water

Formation of Acetals and Ketals from Carbonyl Compounds: A New and Highly Efficient Method Inspired by Cationic Palladium

Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1810-1814 ◽  
Author(s):  
Enoch A. Mensah ◽  
Shawn D. Green ◽  
Jesse West ◽  
Tyler Kindoll ◽  
Brenda Lazaro-Martinez
Keyword(s):  
Efficient Method ◽  
Palladium Catalyst ◽  
Carbonyl Compounds ◽  
Catalyst Loading ◽  
Carbonyl Groups ◽  
Simple Method ◽  
Ambient Temperatures ◽  
Highly Efficient ◽  
Low Catalyst Loading ◽  
Cationic Palladium

The development of a new, highly efficient, and simple method for masking carbonyl groups as acetals and ketals is described. This methodology relies on the nature of the palladium catalyst to direct the acetalization/ketalization reaction. This new protocol is mild and proceed with a very low catalyst loading at ambient temperatures. The method has been extended to a wide variety of different carbonyl compounds with various steric encumbrances to form the corresponding acetals and ketals in excellent yields.

Bis[N,N′-(2-indanolyl)]-1,5-diazacyclooctane as Unique Metal Ligand: Self-Assembly of Palladium Nanoparticles and Catalytic Reactivity on C–C Bond Formation

Synthesis ◽  
2017 ◽  
Vol 50 (05) ◽  
pp. 1097-1104 ◽  
Author(s):  
Katsunori Tanaka ◽  
Katsumasa Fujiki
Keyword(s):  
Heterogeneous Catalyst ◽  
Self Assembly ◽  
Palladium Nanoparticles ◽  
Bond Formation ◽  
Suzuki Coupling ◽  
Catalyst Loading ◽  
Loading Conditions ◽  
Catalytic Reactivity ◽  
Low Catalyst Loading ◽  
Metal Ligand

A previously unreported 1,5-diazacyclooctane-palladium(II) complex was synthesized using bis[N,N′-(2-indanolyl)]-1,5-diazacyclooctane, which was readily prepared via a novel [4+4] homocyclization of the unsaturated imine intermediate generated from acrolein and 1-amino-2-indanol. Interestingly, the 1,5-diazacyclooctane-palladium(II) complex self-assembled to form palladium nanoparticles. This approach readily provided palladium nanoparticles simply by heating a mixture of palladium(II) acetate and bis[N,N′-(2-indanolyl)]-1,4-diazacyclooctane in dichloroethane at mild temperatures. The 1,5-diazacyclooctane-derivative-palladium nanoparticles were successfully deployed in synthetic applications as a heterogeneous catalyst, facilitating Suzuki coupling and a challenging C–C bond formation via C(sp3)–H activation under low catalyst loading conditions.

Y(OTf)3-catalyzed Phosphorylation of 2H-Chromene Hemiacetals with P(O)-H compounds to 2-Phosphorylated 2H-Chromenes

2021 ◽  
Author(s):  
Long Chen ◽  
Shi-Lu Zheng ◽  
Yun-Xiang Zou ◽  
Zhong Wen ◽  
Jiafu Lin ◽  
...  
Keyword(s):  
Catalyst Loading ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Low Catalyst Loading

Facile synthesis of 2-phosphorylated 2H-chromenes has been accomplished herein via a Y(OTf)3-catalyzed dehydrative coupling of 2H-chromene hemiacetals with P(O)-H compounds. This protocol features low catalyst loading, mild reaction conditions, broad...

scholarly journals Enantioselective amination of 4-alkylisoquinoline-1,3(2H,4H)-dione derivatives

RSC Advances ◽  
2020 ◽  
Vol 10 (70) ◽  
pp. 42912-42915
Author(s):  
Cheng Cheng ◽  
Ying-Xian Li ◽  
Xue-Min Jia ◽  
Ji-Quan Zhang ◽  
Yong-Long Zhao ◽  
...  
Keyword(s):  
Catalyst Loading ◽  
Low Catalyst Loading

A mild and efficient enantioselective amination of 4-alkylisoquinoline-1,3(2H,4H)-dione derivatives was established and a broad range of amination products were prepared in excellent yields and ee values with low catalyst loading.

scholarly journals Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction

2018 ◽  
Vol 16 (1) ◽  
pp. 605-613 ◽  
Author(s):  
Vivek Srivastava
Keyword(s):  
Heck Reaction ◽  
Exchange Process ◽  
Reaction Medium ◽  
Analytical Techniques ◽  
Catalyst Loading ◽  
Catalyst Recycling ◽  
Mmt Clay ◽  
Vinyl Phosphonates ◽  
Low Catalyst Loading

AbstractWe successfully synthesized Pd@MMT clay using a cation exchange process. We characterized all the synthesized Pd@MMT clays using sophisticated analytical techniques before testing them as a heterogeneous catalyst for the Mizoroki - Heck reaction (mono and double). The highest yield of the Mizoroki-Heck reaction product was recovered using thermally stable and highly reactive Pd@ MMT-1 clay catalyst in the functionalized ionic liquid reaction medium. We successfully isolated 2-aryl-vinyl phosphonates (mono-Mizoroki-Heck reaction product) and 2,2-diaryl-vinylphosphonates (double-Mizoroki-Heck reaction product) using aryl halides and dialkyl vinyl phosphonates in higher yields. The low catalyst loading, easy recovery of reaction product and 8 times catalyst recycling are the major highlights of this proposed protocol.

Three-Component Synthesis of 4-Arylidene-3-alkylisoxazol-5(4H)-ones in the presence of potassium 2,5-dioxoimidazolidin-1-ide

2021 ◽  
Vol 25 ◽  
Author(s):  
Neda Reihani ◽  
Hamzeh Kiyani
Keyword(s):  
Ethylene Glycol ◽  
Ethyl Acetoacetate ◽  
Reaction Medium ◽  
Hydroxylamine Hydrochloride ◽  
Aromatic Aldehydes ◽  
Catalyst Loading ◽  
Efficient Synthesis ◽  
Current Process ◽  
High Yields ◽  
Low Catalyst Loading

: An efficient synthesis of 4-arylidene-3-alkylisoxazole-5(4H)-ones has been implemented via the three-component cyclocondensation of aryl(heteroaryl)aldehydes with hydroxylamine hydrochloride and β-ketoesters. The potassium 2,5-dioxoimidazolidin-1-ide has been introduced as the new organocatalyst to facilitate of this heterocyclization. In the current process, three starting materials, including substituted benzaldehydes/heterocyclic aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/propyl acetoacetate/butyryl acetoacetate have been successfully used for the synthesize of the number of substituted isoxazole-5(4H)-ones in good to high yields in ethylene glycol as a green reaction medium at 80 ºC. The low catalyst loading is also a main advantage over the some reported catalysts.

Acceleration of Baylis-Hillman reaction using ionic liquid supported organocatalyst

2021 ◽  
Vol 08 ◽  
Author(s):  
Vivek Srivastava
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Reaction Rate ◽  
Reaction Medium ◽  
Catalyst Loading ◽  
Catalyst Recycling ◽  
Catalytic Systems ◽  
Heterogeneous Catalytic ◽  
Highly Active ◽  
Low Catalyst Loading

Background: Baylis-Hillman reaction suffers from the requirement of cheap starting materials, easy reaction protocol, possibility to create the chiral center in the reaction product has increased the synthetic efficacy of this reaction, and high catalyst loading, low reaction rate, and poor yield. Objective: The extensive use of various functional or non-functional ionic liquids (ILs) with organocatalyst increases the reaction rate of various organic transformations as a reaction medium and as a support to anchor the catalysts. Methods: In this manuscript, we have demonstrated the synthesis of quinuclidine-supported trimethylamine-based functionalized ionic liquid as a catalyst for the Baylis-Hillman reaction. Results: We obtained the Baylis-Hillman adducts in good, isolated yield, low catalyst loading, short reaction time, broad substrate scope, accessible product, and catalyst recycling. N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide was also successfully synthesized using CATALYST-3 promoted Baylis-Hillman reaction. Conclusion: We successfully isolated the 25 types of Baylis-Hillman adducts using three different quinuclidine-supported ammonium-based ionic liquids such as Et3AmQ][BF4] (CATALYST-1), [Et3AmQ][PF6] (CATALYST-2), and [TMAAmEQ][NTf2](CATALYST-3) as new and efficient catalysts. Tedious and highly active N-((E,3S,4R)-5-benzylidene-tetrahydro-4-hydroxy-6-oxo-2H-pyran-3-yl) palmitamide derivative was also synthesized using CATALYST-3 followed by Baylis-Hillman reaction. Generally, all the responses demonstrated higher activity and yielded high competition with various previously reported homogenous and heterogeneous Catalytic systems. Easy catalyst and product recovery followed by six catalysts recycling were the added advantages of the prosed catalytic system.

Low Catalyst Loading in the Cross Metathesis of Olefins with Methyl Vinyl Ketone

Synlett ◽  
2013 ◽  
Vol 24 (10) ◽  
pp. 1193-1196 ◽  
Author(s):  
Christian Slugovc ◽  
Muddasar Abbas ◽  
Anita Leitgeb
Keyword(s):  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Catalyst Loading ◽  
Methyl Vinyl ◽  
Cross Metathesis ◽  
The Cross ◽  
Low Catalyst Loading
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