Density Functional Theory Study of the Mechanisms of Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents

2013 ◽  
Vol 117 (4) ◽  
pp. 756-764 ◽  
Author(s):  
Qinghua Ren ◽  
Shuhui Guan ◽  
Feng Jiang ◽  
Jianhui Fang
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Density Functional Theory Study ◽  
Functional Theory ◽  
Cross Coupling Reactions

scholarly journals Radical coupling reactions of piceatannol and monolignols: A density functional theory study

2019 ◽  
Vol 164 ◽  
pp. 12-23 ◽  
Author(s):  
Thomas Elder ◽  
José Carlos del Río ◽  
John Ralph ◽  
Jorge Rencoret ◽  
Hoon Kim ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Coupling Reactions ◽  
Density Functional Theory Study ◽  
Functional Theory ◽  
Radical Coupling

Radical Coupling Reactions in Lignin Synthesis: A Density Functional Theory Study

2012 ◽  
Vol 116 (16) ◽  
pp. 4760-4768 ◽  
Author(s):  
Amandeep K. Sangha ◽  
Jerry M. Parks ◽  
Robert F. Standaert ◽  
Angela Ziebell ◽  
Mark Davis ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Coupling Reactions ◽  
Density Functional Theory Study ◽  
Functional Theory ◽  
Radical Coupling ◽  
Lignin Synthesis

scholarly journals Radical Coupling Reactions of Hydroxystilbene Glucosides and Coniferyl Alcohol: A Density Functional Theory Study

2021 ◽  
Vol 12 ◽  
Author(s):  
Thomas Elder ◽  
Jorge Rencoret ◽  
José C. del Río ◽  
Hoon Kim ◽  
John Ralph
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Biosynthetic Pathway ◽  
Cross Coupling ◽  
Coniferyl Alcohol ◽  
Coupling Reactions ◽  
Functional Theory ◽  
Radical Coupling ◽  
Synthetic Models

The monolignols, p-coumaryl, coniferyl, and sinapyl alcohol, arise from the general phenylpropanoid biosynthetic pathway. Increasingly, however, authentic lignin monomers derived from outside this process are being identified and found to be fully incorporated into the lignin polymer. Among them, hydroxystilbene glucosides, which are produced through a hybrid process that combines the phenylpropanoid and acetate/malonate pathways, have been experimentally detected in the bark lignin of Norway spruce (Picea abies). Several interunit linkages have been identified and proposed to occur through homo-coupling of the hydroxystilbene glucosides and their cross-coupling with coniferyl alcohol. In the current work, the thermodynamics of these coupling modes and subsequent rearomatization reactions have been evaluated by the application of density functional theory (DFT) calculations. The objective of this paper is to determine favorable coupling and cross-coupling modes to help explain the experimental observations and attempt to predict other favorable pathways that might be further elucidated via in vitro polymerization aided by synthetic models and detailed structural studies.

scholarly journals Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes

Synthesis ◽  
2019 ◽  
Vol 52 (04) ◽  
pp. 565-573 ◽  
Author(s):  
Alasdair K. Cooper ◽  
Paul M. Burton ◽  
David J. Nelson
Keyword(s):  
Functional Groups ◽  
Density Functional ◽  
Aryl Halide ◽  
Cross Coupling ◽  
Density Functional Theory Calculations ◽  
Detailed Comparison ◽  
Coupling Reactions ◽  
Functional Theory ◽  
Cross Coupling Reactions

A detailed comparison of the effect of coordinating functional groups on the performance of Suzuki–Miyaura reactions catalysed by nickel and palladium is reported, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has effects on cross-coupling reactions that range from a slight improvement in yield to the complete cessation of the reaction. In contrast, palladium does not interact sufficiently strongly with these functional groups to induce selectivity in cross-coupling reactions; the selectivity of palladium-catalysed cross-coupling reactions is predominantly governed by aryl halide electronic properties.

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