Copper Immobilization on Fe3O4@Agar: An Efficient Superparamagnetic Nanocatalyst for Green Ullmann-Type Cross-Coupling Reaction of Primary and Secondary Amines with Aryl Iodide Derivatives

2021 ◽  
Author(s):  
Kimia Hoseinzade ◽  
Seyed Ali Mousavi-Mashhadi ◽  
Ali Shiri
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Secondary Amines ◽  
Aryl Iodide ◽  
Cross Coupling Reaction ◽  
Primary And Secondary Amines

scholarly journals Copper Immobilization on Fe3o4@Agar: An Efficient Superparamagnetic Nanocatalyst for Green Buchwald-Hartwig Cross-coupling Reaction of Primary and Secondary Amines With Aryl Iodide Derivatives

2021 ◽  
Author(s):  
Kimia Hoseinzade ◽  
Seyed Ali Mousavi-Mashhadi ◽  
Ali Shiri
Keyword(s):  
Electron Microscopy ◽  
Magnetic Nanoparticles ◽  
Inductively Coupled Plasma ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Secondary Amines ◽  
Aryl Iodide ◽  
X Ray ◽  
Inductively Coupled ◽  
Cross Coupling Reaction

Abstract Immobility of copper on magnetic nanoparticles was performed using surface rectification of Fe3O4 with Agar. The magnetic Fe3O4@Agar-Cu nanocatalyst was prepared and entirely characterized by different analyses such as Fourier transform infrared (FT‐IR), X‐ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), energy dispersive X-ray (EDX), thermogravimetric (TGA), and inductively coupled plasma (ICP). The nanocatalyst was applied in C-N bond formation through the cross-coupling reaction of aryl halides with primary or secondary amines in water as a green medium known as the Buchwald-Hartwig reaction. The results of the Buchwald-Hartwig reaction by Fe3O4@Agar-Cu magnetic nanoparticles as catalyst demonstrate excellent activity and stability in water. Moreover, this catalyst can be recycled several times without considerable loss in its activity.

Synthesis of 4,4-Difluoro-a-tocopherol Using a Cross-coupling Reaction of Bromodifluoroacetate with Aryl Iodide in the Presence of Copper Powder

Heterocycles ◽  
2002 ◽  
Vol 56 (1-2) ◽  
pp. 403 ◽  
Author(s):  
Itsumaro Kumadaki ◽  
Kazuyuki Sato ◽  
Takashi Nishimoto ◽  
Kei Tamoto ◽  
Masaaki Omote ◽  
...  
Keyword(s):  
Copper Powder ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Iodide ◽  
Cross Coupling Reaction

scholarly journals Synthesis and antifungal properties of papulacandin derivatives

2012 ◽  
Vol 8 ◽  
pp. 732-737 ◽  
Author(s):  
Marjolein van der Kaaden ◽  
Eefjan Breukink ◽  
Roland J Pieters
Keyword(s):  
Biological Activity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Side Chain ◽  
Aryl Iodide ◽  
Glucan Synthase ◽  
Cross Coupling Reaction ◽  
Acyl Side Chain ◽  
Palladium Catalyzed ◽  
Derivatives Of

Derivatives of an antifungal agent that targets the β-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal silanolate and an aryl iodide followed by an oxidative spiroketalization. Four different variants were made, differing in the nature of the acyl side chain with respect to the length, and in the number and stereochemistry of the double bonds. Moderate biological activity was observed for the derivatives with a side chain based on palmitic acid and linoleic acid.

Ni-Catalyzed Deamination Cross-Electrophile Coupling of Katritzky Salts with Halides via C–N Bond Activation

2019 ◽  
Author(s):  
Shengyang Ni ◽  
Chunxiao Li ◽  
Jianlin Han ◽  
Yu Mao ◽  
Yi Pan
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Aryl Iodide ◽  
Cross Coupling Reaction ◽  
New Strategy ◽  
The Cross

This work describes the first Ni-catalyzed cross-electrophile coupling of alkylpyridinium salts, derived from the corresponding amines, with aryl iodide, bromoalkyne or bromoalkyl coupling partners. C(sp)-C(sp<sup>3</sup>), C(sp<sup>2</sup>)-C(sp<sup>3</sup>) and C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond formation was achieved to afford a variety of synthetically useful arenes, alkynes and alkanes in good yields from<b>2</b>-<b>33</b>. The advantages of the methodology are showcased in the two-step synthesis of the key lactonic moiety of (+)-Compactin and (+)-Mevinolin from commercially available starting materials. A one-pot procedure without isolation of alkylpyridinium tetrafluoroborate salt was also demonstrated to be successful. This work represents a new strategy for the cross-coupling reaction of two electrophiles, and also provides a complementary and highly valuable vista for the current methodologies of alkyl arene/alkyne/alkane synthesis.

scholarly journals Oxidative Coupling of Aryl Boronic Acids with Aryl- and Alkylamines via Cooperative Photoredox and Copper Catalysis

2019 ◽  
Author(s):  
Jennifer Marshall ◽  
Juliana O'Brien ◽  
Andrew Wommack
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Secondary Amines ◽  
Copper Catalysis ◽  
Ambient Atmosphere ◽  
Aerobic Conditions ◽  
Cross Coupling Reaction

<p>Copper(II)-catalyzed oxidative cross-couplings of aryl boronic acids with aryl- and alkylamines have been accomplished across a range of substrates in the presence of a ruthenium(II)-photoredox cocatalyst under mild aerobic conditions. This modified C−N cross-coupling reaction allows the incorporation of alkylamines to both electron poor− and electron-rich aryl boronic acids with low photocatalyst loadings and under ambient atmosphere. The coupling protocol provides secondary amines in yields of 63-90% during the safe, procedurally improved process. </p>

Ni-Catalyzed Deamination Cross-Electrophile Coupling of Katritzky Salts with Halides via C–N Bond Activation

2019 ◽  
Author(s):  
Shengyang Ni ◽  
Chunxiao Li ◽  
Jianlin Han ◽  
Yu Mao ◽  
Yi Pan
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Aryl Iodide ◽  
Cross Coupling Reaction ◽  
New Strategy ◽  
The Cross

This work describes the first Ni-catalyzed cross-electrophile coupling of alkylpyridinium salts, derived from the corresponding amines, with aryl iodide, bromoalkyne or bromoalkyl coupling partners. C(sp)-C(sp<sup>3</sup>), C(sp<sup>2</sup>)-C(sp<sup>3</sup>) and C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond formation was achieved to afford a variety of synthetically useful arenes, alkynes and alkanes in good yields from<b>2</b>-<b>33</b>. The advantages of the methodology are showcased in the two-step synthesis of the key lactonic moiety of (+)-Compactin and (+)-Mevinolin from commercially available starting materials. A one-pot procedure without isolation of alkylpyridinium tetrafluoroborate salt was also demonstrated to be successful. This work represents a new strategy for the cross-coupling reaction of two electrophiles, and also provides a complementary and highly valuable vista for the current methodologies of alkyl arene/alkyne/alkane synthesis.

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