Pd-Catalyzed diastereoselective [3 + 2] cycloaddition of vinylcyclopropanes with sulfamate-derived cyclic imines

2018 ◽  
Vol 16 (26) ◽  
pp. 4881-4887 ◽  
Author(s):  
Qijun Wang ◽  
Chang Wang ◽  
Wangyu Shi ◽  
Yumei Xiao ◽  
Hongchao Guo
Keyword(s):  
Cycloaddition Reaction ◽  
Mild Conditions ◽  
Palladium Catalyzed

The palladium-catalyzed diastereoselective [3 + 2] cycloaddition reaction of vinylcyclopropanes with sulfamate-derived cyclic imines worked efficiently under mild conditions, providing sulfamate-fused pyrrolidines in good to excellent yields.

Palladium-catalyzed [4 + 3] dearomatizing cycloaddition reaction of N-iminoquinolinium ylides

2020 ◽  
Vol 7 (18) ◽  
pp. 2612-2617
Author(s):  
Wenhao Dai ◽  
Chunpu Li ◽  
Yichu Liu ◽  
Xu Han ◽  
Xingjun Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Cycloaddition Reaction ◽  
Membered Ring ◽  
Efficient Approach ◽  
Mild Conditions ◽  
Palladium Catalyzed

An efficient approach to obtain saturated seven-membered ring containing three heteroatoms has been developed by using a palladium-catalyzed [4 + 3] dearomatizing cycloaddition. This approach features mild conditions and good functional group tolerance.

The Synthesis and Electroluminescence Properties of 4-Benzofuranyl-1,8-Naphthalimide Derivatives

2012 ◽  
Vol 557-559 ◽  
pp. 1031-1036 ◽  
Author(s):  
Jian Xin Yang ◽  
Xiang Hui Wang
Keyword(s):  
Absorption Spectra ◽  
Fluorescence Spectra ◽  
Cycloaddition Reaction ◽  
Emission Spectra ◽  
Luminescent Properties ◽  
Quantum Yields ◽  
Absorption And Fluorescence Spectra ◽  
Maximum Brightness ◽  
Maximum Emission ◽  
Mild Conditions

A series of fluorescence compounds, 4-benzofuranyl-1,8-naphthalimides, were prepared through cycloaddition reaction from 4-ethynyl-1,8-naphthalimides and o-iodophenols which catalyzed by a Pd(PPh3)2Cl2 / CuI system under mild conditions. The intermediate material, 4-ethynyl-1,8- naphthalimide, was synthesized from 4-bromo-1,8- naphthalimide and trimethylsilyl- acetylene. The absorption and fluorescence spectra of 4-benzofuranyl-1,8- naphthalimides were studied and the quantum yields were measured. The maximum UV/vis absorption spectra were in the range of 375-400 nm and the maximum emission spectra were in the range of 470-510 nm. The electro- luminescent properties were also mensurated through a doped electroluminescent device which contains 1% 1,8-naphthalimides and 99% CBP (4,4'-N,N'-dicarbazole-biphenyl), It’s shown the maximum brightness reached 3700 cd/ m2 at 22.5V.

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>

scholarly journals Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides

2016 ◽  
Vol 7 (6) ◽  
pp. 3757-3762 ◽  
Author(s):  
Jiang Wu ◽  
Yafei Liu ◽  
Changhui Lu ◽  
Qilong Shen
Keyword(s):  
Mild Conditions ◽  
Aryl Iodides ◽  
Palladium Catalyzed

A palladium-catalyzed difluoromethylthiolation of heteroaryl halides and triflates under mild conditions was described.

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

2017 ◽  
Vol 41 (1) ◽  
pp. 372-376 ◽  
Author(s):  
Jinyi Song ◽  
Hongyan Zhao ◽  
Yang Liu ◽  
Huatao Han ◽  
Zhuofei Li ◽  
...  
Keyword(s):  
High Activity ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bidentate Ligands ◽  
Aryl Chlorides ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

A series of N,O-bidentate ligands were synthesized and studied as high activity ligands for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions.

Palladium-Catalyzed Desulfurative Hiyama Coupling of Thioureas to Achieve Amides via Selective C–N Bond Cleavage

Synthesis ◽  
2021 ◽  
Author(s):  
Zhuo Zeng ◽  
Zhanyu He ◽  
Chu Yan ◽  
Mei Zhang ◽  
Majeed Irfan ◽  
...  
Keyword(s):  
Good Yield ◽  
Bond Cleavage ◽  
New Approach ◽  
Mild Conditions ◽  
Palladium Catalyzed

AbstractPalladium-catalyzed Hiyama coupling of active thioureas via selective C–N bond cleavage is reported. Notably, the new approach employed active thioureas as coupling partners in the presence of arylsilanes to give amides in good yield. Further, this strategy, which utilized CuF2 as a key oxidant and activator, afforded various amide products under mild conditions and an easy to handle procedure without extra base.

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4215-4230 ◽  
Author(s):  
Adesh Kumar Singh ◽  
Rapelly Venkatesh ◽  
Jeyakumar Kandasamy
Keyword(s):  
Room Temperature ◽  
Stereospecific Synthesis ◽  
One Pot ◽  
Tert Butyl ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
Aryl Glycosides

The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF4 under mild conditions. This one-pot method stereospecifically provides α- and β-aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

Palladium-catalyzed allylic C–H oxidation under simple operation and mild conditions

2019 ◽  
Vol 17 (12) ◽  
pp. 3103-3107 ◽  
Author(s):  
Yunlong Guo ◽  
Zengming Shen
Keyword(s):  
Simple System ◽  
Allylic Alcohols ◽  
Bond Functionalization ◽  
Simple Operation ◽  
Mild Conditions ◽  
Palladium Catalyzed

We discovered an effective and simple system (Pd/BQ/air/r.t.) for making allylic alcohols through Pd-catalyzed allylic C–H bond functionalization.

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