scholarly journals Computational study of productive and non-productive cycles in fluoroalkene metathesis

2015 ◽  
Vol 11 ◽  
pp. 2150-2157 ◽  
Author(s):  
Markéta Rybáčková ◽  
Jan Hošek ◽  
Ondřej Šimůnek ◽  
Viola Kolaříková ◽  
Jaroslav Kvíčala
Keyword(s):  
Computational Study ◽  
Catalytic Cycle ◽  
Dft Study ◽  
Cross Metathesis ◽  
High Preference ◽  
The Cross

A detailed DFT study of the mechanism of metathesis of fluoroethene, 1-fluoroethene, 1,1-difluoroethene, cis- and trans-1,2-difluoroethene, tetrafluoroethene and chlorotrifluoroethene catalysed with the Hoveyda–Grubbs 2nd generation catalyst was performed. It revealed that a successful metathesis of hydrofluoroethenes is hampered by a high preference for a non-productive catalytic cycle proceeding through a ruthenacyclobutane intermediate bearing fluorines in positions 2 and 4. Moreover, the calculations showed that the cross-metathesis of perfluoro- or perhaloalkenes should be a feasible process and that the metathesis is not very sensitive to stereochemical issues.

Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst

2015 ◽  
Vol 68 (12) ◽  
pp. 1815 ◽  
Author(s):  
Steven-Alan G. Abel ◽  
Wesley J. Olivier ◽  
Richard L. Pederson ◽  
Alex C. Bissember ◽  
Jason A. Smith
Keyword(s):  
The Self ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Metathesis Catalyst ◽  
The Cross

(R)-Harmonine was synthesised in 15 % overall yield via a six-step sequence exploiting a Z-selective cross-metathesis reaction as its centrepiece. By this strategy, the cis-olefin present in the target could be installed exclusively. The use of an alcohol and an ester as the amine precursors was crucial for isolating the cross-metathesis product from the self-metathesis products. This method was also used to prepare two novel analogues of harmonine.

DFT study of the full catalytic cycle for the propene hydroformylation catalyzed by a heterobimetallic HPt(SnCl3)(PH3)2model catalyst

2010 ◽  
pp. NA-NA ◽  
Author(s):  
Júlio C. S. da Silva ◽  
Roberta P. Dias ◽  
Wagner B. de Almeida ◽  
Willian R. Rocha
Keyword(s):  
Catalytic Cycle ◽  
Dft Study

Catalytic Cycle for N–CN Bond Cleavage by Molybdenum Silyl Catalyst: A DFT Study

2013 ◽  
Vol 32 (9) ◽  
pp. 2725-2735 ◽  
Author(s):  
AbdelRahman A. Dahy ◽  
Nobuaki Koga ◽  
Hiroshi Nakazawa
Keyword(s):  
Bond Cleavage ◽  
Catalytic Cycle ◽  
Dft Study

Low Catalyst Loading in the Cross Metathesis of Olefins with Methyl Vinyl Ketone

Synlett ◽  
2013 ◽  
Vol 24 (10) ◽  
pp. 1193-1196 ◽  
Author(s):  
Christian Slugovc ◽  
Muddasar Abbas ◽  
Anita Leitgeb
Keyword(s):  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Catalyst Loading ◽  
Methyl Vinyl ◽  
Cross Metathesis ◽  
The Cross ◽  
Low Catalyst Loading

scholarly journals Equilibrium data for the cross-metathesis of methyl oleate with cinnamaldehyde

Data in Brief ◽  
2018 ◽  
Vol 20 ◽  
pp. 190-195
Author(s):  
Pablo D. Nieres ◽  
Andrés F. Trasarti ◽  
Carlos R. Apesteguía
Keyword(s):  
Methyl Oleate ◽  
Cross Metathesis ◽  
Equilibrium Data ◽  
The Cross

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

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3612 ◽  
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.

Regulation of the degree of blockiness of the norbornene–cyclooctene copolymer synthesized via the cross-metathesis reaction

2016 ◽  
Vol 58 (3) ◽  
pp. 292-297 ◽  
Author(s):  
Yu. I. Denisova ◽  
M. L. Gringolts ◽  
L. B. Krentsel’ ◽  
G. A. Shandryuk ◽  
A. D. Litmanovich ◽  
...  
Keyword(s):  
Metathesis Reaction ◽  
Cross Metathesis ◽  
The Cross

scholarly journals Stereoretention in styrene heterodimerisation promoted by one-electron oxidants

2020 ◽  
Vol 11 (34) ◽  
pp. 9309-9324
Author(s):  
Xinglong Zhang ◽  
Robert S. Paton
Keyword(s):  
Computational Study ◽  
Catalytic Cycle

A computational study details the mechanism, catalytic cycle and origins of stereoselectivity underlying hole-catalyzed intermolecular alkene heterodimerisation to give unsymmetrical, tetra-substituted cyclobutanes.

scholarly journals Divergent Reactivity of Indole-Tethered Ynones with Silver(I) and Gold(I) Catalysts: A Combined Synthetic and Computational Study

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4829-4836 ◽  
Author(s):  
Jason Lynam ◽  
Richard Taylor ◽  
William Unsworth ◽  
John Liddon ◽  
James Rossi-Ashton ◽  
...  
Keyword(s):  
Ring Opening ◽  
Computational Study ◽  
Dft Study ◽  
Migration Mechanism ◽  
Catalyst Systems

A combined synthetic and computational (DFT) study has been performed to account for the divergent reactivity of indole-tethered ynones when treated with Ag(I) and Au(I) catalysts. The two catalyst systems deliver spirocyclic indolenines and carbazoles, respectively, from the same precursors, with the reaction outcomes believed to be a result of differences in the rates of a key protodemetalation step. A ring-opening/ring-closing isomerisation process is proposed to enable the interconversion of spirocyclic and C-2 annulated indole intermediates, in contrast to the 1,2-migration mechanism tentatively proposed in previous studies.

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