Palladium-Catalyzed C–H Bond Monofluorination of 2-Arylbenzo[d]oxazinone Using Nitrate as Crucial Promoter

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1578-1584 ◽  
Author(s):  
Xu-Qin Li ◽  
Huu-Manh Vu ◽  
Fei-Wu Chen
Keyword(s):  
Functional Groups ◽  
Palladium Catalysis ◽  
Environmentally Friendly ◽  
Palladium Catalyzed ◽  
Plausible Mechanism

Monofluorination of 2-arylbenzo[d]oxazinones with N-fluorobenzenesulfonimide (NFSI) was achieved by palladium catalysis in moderate to good yields. Promoted by nitrate, the reaction provides an economic and environmentally friendly strategy. The synthesis of monofluorinated 2-arylbenzo[d]oxazinones has good compatibility with many common functional groups. The plausible mechanism of this monofluorination is discussed.

Access to Chiral γ-Butenolides via Palladium-Catalyzed Asymmetric Allylic C-H Alkylation of 1,4-Dienes

2021 ◽  
Author(s):  
Zhen-Yao Dai ◽  
Pu-Sheng Wang ◽  
Liu-zhu Gong
Keyword(s):  
Functional Groups ◽  
Palladium Catalysis ◽  
Mild Conditions ◽  
Palladium Catalyzed

Asymmetric allylic C-H alkylation of 1,4-pentadienes with α-angelica lactones has been developed by tri-axial phosphoramidite-palladium catalysis. This reaction can tolerate a range of functional groups under mild conditions, furnishing versatile...

Temporary (PO) directing group enabled carbazole ortho arylation via palladium catalysis

2021 ◽  
Vol 57 (16) ◽  
pp. 2021-2024
Author(s):  
Zhi-Chao Qi ◽  
Qin-Xin Lou ◽  
Yuan Niu ◽  
Shang-Dong Yang
Keyword(s):  
Palladium Catalysis ◽  
Palladium Catalyzed ◽  
Directing Group

An efficient palladium-catalyzed, temporary P(O) directing group assisted C–H bond arylation of carbazoles was achieved, accompanied by the directing group being self-shed spontaneously.

Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zheng-Yang Gu ◽  
Yang Wu ◽  
Feng Jin ◽  
Bao Xiaoguang ◽  
Ji-Bao Xia
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalysis ◽  
Computational Studies ◽  
Organic Azides ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
And Control

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

scholarly journals Cycloaddition of Thiourea- and Guanidine-Substituted Furans to Dienophiles: A Comparison of the Environmentally-Friendly Methods

2020 ◽  
Vol 3 (1) ◽  
pp. 57
Author(s):  
Luka Barešić ◽  
Davor Margetić ◽  
Zoran Glasovac
Keyword(s):  
High Pressure ◽  
Functional Groups ◽  
Organic Synthesis ◽  
High Speed ◽  
Environmentally Friendly ◽  
Microwave Assisted ◽  
Pressure Synthesis ◽  
Ultrasound Assisted ◽  
Substituted Furans ◽  
Guanidine Moiety

The cycloaddition strategy was employed in order to obtain a 7-oxanorbornene framework substituted with a guanidine moiety or its precursor functional groups: protected amine or thiourea. In order to optimize the conditions for the cycloaddition, several environmentally-friendly methods—microwave assisted organic synthesis, high pressure synthesis, high speed vibrational milling, and ultrasound assisted synthesis—were employed. The outcomes of the cycloaddition reactions were interpreted in terms of endo/exo selectivity, the conversion of the reactants to the product, and the isolated yields. In general, our results indicated the HP and HSVM approaches as the methods of choice to give good yields and conversions.

Palladium-catalyzed paraformaldehyde insertion: a three-component synthesis of benzofurans

2016 ◽  
Vol 14 (10) ◽  
pp. 2819-2823 ◽  
Author(s):  
Xiufang Cheng ◽  
Yi Peng ◽  
Jun Wu ◽  
Guo-Jun Deng
Keyword(s):  
Palladium Catalysis ◽  
Phenacyl Bromides ◽  
Palladium Catalyzed

2-Aroylbenzofurans were prepared from 2-bromophenols, phenacyl bromides and paraformaldehyde under palladium catalysis conditions.

scholarly journals Palladium-Catalyzed [3+2] Cycloaddition via Two-Fold 1,3-C(sp3)−H Activation

2020 ◽  
Author(s):  
Hojoon Park ◽  
jin-quan yu
Keyword(s):  
Functional Groups ◽  
Sulfonic Acid ◽  
Cycloaddition Reaction ◽  
Wide Range ◽  
Leaving Group ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
Overall Efficiency ◽  
Weak Coordination ◽  
Single Reaction

<div>Cycloaddition reactions provide an expeditious route to construct ring systems in a highly convergent and stereoselective manner. For a typical cycloaddition reaction to occur, however, the installation of multiple reactive functional groups (π-bonds, leaving group, etc.) are required within the substrates, compromising the overall efficiency or scope of the cycloaddition reaction. Here, we report a palladium-catalyzed [3+2] reaction that utilizes C(sp<sup>3</sup>)–H activation to generate the three-carbon unit for formal cycloaddition with maleimides. We implemented a strategy where the initial C(sp<sup>3</sup>)–H activation/olefin insertion would trigger a relayed, second remote C(sp<sup>3</sup>)–H activation to complete a formal [3+2] cycloaddition. The diastereoselectivity profile of this reaction resembles that of a typical pericyclic cycloaddition reaction in that the relationships between multiple stereocenters are exquisitely controlled in a single reaction. The key to success was the use of weakly coordinating amides as the directing group, as undesired Heck or alkylation pathways were preferred with other types of directing groups. The use of the pyridine-3-sulfonic acid ligands is critical to enable C(sp<sup>3</sup>)–H activation directed by this weak coordination. The method is compatible with a wide range of amide substrates, including lactams, which lead to novel spiro-bicyclic products. The [3+2] product is also shown to undergo a reductive desymmetrization process to access chiral cyclopentane bearing multiple stereocenters with excellent enantioselectivity.</div>

An Environmentally Friendly Technology for Biomass Production Hydorchar from Renewable Resources

2013 ◽  
Vol 726-731 ◽  
pp. 634-637 ◽  
Author(s):  
Yan Qiu Lei ◽  
Hai Quan Su
Keyword(s):  
Activated Carbon ◽  
Reaction Time ◽  
Adsorption Capacity ◽  
Functional Groups ◽  
Biomass Production ◽  
Renewable Resources ◽  
Environmentally Friendly ◽  
Hydrothermal Carbonization ◽  
Removal Rates

A green and sustainable route for preparation of hydrochars from cornstalk by hydrothermal carbonization (200°C) was described. The morphology of the hydrochars changed with reaction time increased, the surface of the materials contained a large number of functional groups, showed higher adsorption capacity for Cr (VI) than activated carbon and the removal rates of Cr (VI) were 67% and 29% respectively (pH=1, 20°C).

Palladium-Catalyzed Divergent Cycloisomerization of 1,6-Enynes Controlled by Functional Groups for the Synthesis of Pyrroles, Cyclopentenes, and Tetrahydropyridines

2021 ◽  
Author(s):  
Xiao-Feng Xia ◽  
Linglong Ding ◽  
Yi-Hui Deng ◽  
Tian-Yu Sun ◽  
Dawei Wang ◽  
...  
Keyword(s):  
Functional Groups ◽  
Palladium Catalyzed

Controlling by functional groups, catalytic divergent cycloisomerization of 1,6-enynes is achieved for the synthesis of pyrrole, cyclopentene, and tetrahydropyridine derivatives using the combination of a Pd(0) catalyst with glucose. Detailed...

scholarly journals Palladium(II)-Catalyzed C(sp3)–H Activation of N,O-Ketals towards a Method for the β-Functionalization of Ketones

Synlett ◽  
2019 ◽  
Vol 30 (04) ◽  
pp. 454-458 ◽  
Author(s):  
Danny Ho ◽  
Jonas Calleja ◽  
Matthew Gaunt
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Building Blocks ◽  
Activation Pathway ◽  
Bond Forming ◽  
Aliphatic Ketones ◽  
Palladium Catalyzed

A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp3 C–H activation pathway is reported. An N,O-ketal directs an aliphatic C–H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carboxylic acids. This C–C bond-forming reaction is tolerant of a range of functional groups, enabling the synthesis of a range of synthetically important building blocks. Furthermore, the concepts underlying this transformation have also enabled the development of a related C–H alkenylation process to highly functionalised heterocycles.

Palladium-catalyzed simple and efficient hydrogenative cleavage of azo compounds using recyclable polymer-supported formate

2005 ◽  
Vol 83 (5) ◽  
pp. 517-520 ◽  
Author(s):  
Keelara Abiraj ◽  
Gejjalagere R Srinivasa ◽  
D Channe Gowda
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Azo Compounds ◽  
Catalytic Transfer Hydrogenation ◽  
Palladium Catalyzed ◽  
Catalytic Transfer ◽  
Polymer Supported

Palladium-catalyzed room temperature transfer hydrogenation of azo compounds using recyclable polymer-supported formate as the hydrogen donor produces corresponding amine(s) in excellent yields (88%–98%). This method was found to be highly facile with selectivity over a number of other functional groups such as halogen, alkene, nitrile, carbonyl, amide, methoxy, and hydroxyl.Key words: azo compounds, catalytic transfer hydrogenation, polymer-supported formate, 10% Pd-C, amines.

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