Mechanism of Pd-catalyzed acylation/alkenylation of aryl iodide: a DFT study

The detailed mechanism of the Pd(0)-catalyzed cross-coupling of aryl iodide, benzoic anhydride and ethyl acrylate was clarified by theoretical methods.

Download Full-text

A DFT Study on FeI/FeII/FeIII Mechanism of the Cross-Coupling between Haloalkane and Aryl Grignard Reagent Catalyzed by Iron-SciOPP Complexes

Molecules ◽

10.3390/molecules25163612 ◽

2020 ◽

Vol 25 (16) ◽

pp. 3612 ◽

Cited By ~ 1

Author(s):

Akhilesh Sharma ◽

Masaharu Nakamura

Keyword(s):

Density Functional ◽

Molecular Mechanic ◽

Coupling Reaction ◽

Cross Coupling ◽

Dft Study ◽

Reaction Pathways ◽

Hydrogen Elimination ◽

Cross Coupling Reaction ◽

The Cross ◽

A Chain

To explore plausible reaction pathways of the cross-coupling reaction between a haloalkane and an aryl metal reagent catalyzed by an iron–phosphine complex, we examine the reaction of FeBrPh(SciOPP) 1 and bromocycloheptane employing density functional theory (DFT) calculations. Besides the cross-coupling, we also examined the competitive pathways of β-hydrogen elimination to give the corresponding alkene byproduct. The DFT study on the reaction pathways explains the cross-coupling selectivity over the elimination in terms of FeI/FeII/FeIII mechanism which involves the generation of alkyl radical intermediates and their propagation in a chain reaction manner. The present study gives insight into the detailed molecular mechanic of the cross-coupling reaction and revises the FeII/FeII mechanisms previously proposed by us and others.

Download Full-text

Long-Distance Chirality Transfer from P-Ligand to Prochiral Dihydrosilanes via Pd(II) Aryl Iodide Complex in Pd-Catalyzed Silylation of Aryl Iodide: A DFT Study

The Journal of Organic Chemistry ◽

10.1021/acs.joc.0c00202 ◽

2020 ◽

Vol 85 (22) ◽

pp. 14360-14368

Author(s):

Jing-Jing Yang ◽

Zheng Xu ◽

Yi-Xue Nie ◽

Si-Qi Lu ◽

Jin Zhang ◽

...

Keyword(s):

Dft Study ◽

Long Distance ◽

Aryl Iodide ◽

Chirality Transfer ◽

Iodide Complex

Download Full-text

ChemInform Abstract: Efficient Cobalt-Catalyzed C-N Cross-Coupling Reaction Between Benzamide and Aryl Iodide in Water.

ChemInform ◽

10.1002/chin.201509043 ◽

2015 ◽

Vol 46 (9) ◽

pp. no-no

Author(s):

Bryan Yong-Hao Tan ◽

Yong-Chua Teo

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Aryl Iodide ◽

Cross Coupling Reaction

Download Full-text

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

Heterocycles ◽

10.3987/com-01-s(k)61 ◽

2002 ◽

Vol 56 (1-2) ◽

pp. 403 ◽

Cited By ~ 9

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

Download Full-text

A mechanistic study on Cu(i) catalyzed carboxylation of the C–F bond with CO2: a DFT study

Organic & Biomolecular Chemistry ◽

10.1039/d0ob01414a ◽

2020 ◽

Vol 18 (44) ◽

pp. 9065-9071

Author(s):

Jiao Liu ◽

Wan Nie ◽

Haizhu Yu ◽

Jing Shi

Keyword(s):

Theoretical Calculations ◽

Dft Study ◽

Mechanistic Study ◽

Detailed Mechanism ◽

Excellent Method

Cu(i) catalyzed carboxylation of the C–F bond is an excellent method for construction of complex fluoroacrylate compounds with high regioselectivity. Here, theoretical calculations were carried out to investigate the detailed mechanism and origin of regioselectivity.

Download Full-text

Synthesis and antifungal properties of papulacandin derivatives

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.8.82 ◽

2012 ◽

Vol 8 ◽

pp. 732-737 ◽

Cited By ~ 22

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.

Download Full-text