scholarly journals Grubbs Cross-Metathesis Pathway for a Scalable Synthesis of γ-Keto-α,β-unsaturated Esters

2014 ◽  
Vol 79 (3) ◽  
pp. 1467-1472 ◽  
Author(s):  
Reji N. Nair ◽  
Thomas D. Bannister
Keyword(s):  
Unsaturated Esters ◽  
Cross Metathesis ◽  
Scalable Synthesis

Synthesis of Substituted β‐Functionalised Styrenes by Microwave‐Assisted Olefin Cross‐Metathesis and Scalable Synthesis of Apremilast

ChemCatChem ◽  
2019 ◽  
Vol 11 (23) ◽  
pp. 5808-5813 ◽  
Author(s):  
Anupam Jana ◽  
Grzegorz Krzysztof Zieliński ◽  
Sylwia Czarnocka‐Śniadała ◽  
Krzysztof Grudzień ◽  
Dominika Podwysocka ◽  
...  
Keyword(s):  
Microwave Assisted ◽  
Cross Metathesis ◽  
Scalable Synthesis

scholarly journals Synthesis of Linear (Z )-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile

2016 ◽  
Vol 55 (42) ◽  
pp. 13210-13214 ◽  
Author(s):  
Elsie C. Yu ◽  
Brett M. Johnson ◽  
Erik M. Townsend ◽  
Richard R. Schrock ◽  
Amir H. Hoveyda
Keyword(s):  
Unsaturated Esters ◽  
Cross Metathesis

Synthesis of Linear (Z )-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile

2016 ◽  
Vol 128 (42) ◽  
pp. 13404-13408 ◽  
Author(s):  
Elsie C. Yu ◽  
Brett M. Johnson ◽  
Erik M. Townsend ◽  
Richard R. Schrock ◽  
Amir H. Hoveyda
Keyword(s):  
Unsaturated Esters ◽  
Cross Metathesis

ChemInform Abstract: Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

ChemInform ◽  
2016 ◽  
Vol 47 (52) ◽  
Author(s):  
Elsie C. Yu ◽  
Brett M. Johnson ◽  
Erik M. Townsend ◽  
Richard R. Schrock ◽  
Amir H. Hoveyda
Keyword(s):  
Unsaturated Esters ◽  
Cross Metathesis

Synthesis of Unsaturated Esters by Cross-Metathesis of Terpenes and Natural Rubber Using Ru-Alkylidene Catalysts

2019 ◽  
Vol 23 (12) ◽  
pp. 1356-1364
Author(s):  
Araceli Martínez ◽  
Mikhail A. Tlenkopatchev ◽  
Selena Gutiérrez ◽  
Manuel Burelo ◽  
Joel Vargas ◽  
...  
Keyword(s):  
Natural Rubber ◽  
Unsaturated Ester ◽  
Low Molecular Weight ◽  
Diethyl Maleate ◽  
Metathesis Reaction ◽  
Unsaturated Esters ◽  
Cross Metathesis ◽  
Dimethyl Maleate ◽  
The Cross ◽  
Low Activity

This study reports the cross-metathesis of bicyclic β-pinene, acyclic cis-3- methylpent-2-ene terpenes and the natural rubber with functionalized olefins, a route for the functionalization of the carbon-carbon double bond of natural products to obtain aliphatic unsaturated esters. The production of unsaturated esters from β-pinene and cis-3- methylpent-2-ene via cross-metathesis reaction with dimethyl maleate and diethyl maleate in the presence of the ruthenium-alkylidene [Ru(Cl)2(=CHPh)(1,3-bis(2,4,6- trimethylphenyl)-2-imidazolidinylidene)(PCy3)] (I), [Ru(Cl)2(=CH(o-isopropoxyphenylmethylene))( 1,3-bis(2,4,6-trimethylphenyl) -2-imidazolidinylidene)] (II) and rutheniumvinylidene [RuCl2(=C=CH(p-C6H4CF3))(PCy3)2] (III) was carried out. Results showed that the reaction of β-pinene with diethyl maleate using II catalyst produced unsaturated esters with 43 % selectivity. I and III catalysts showed low activity toward the cross-metathesis of β-pinene and dimethyl maleate. A survey about the cross-metathesis of acyclic cis-3-methylpent-2-ene with diethyl maleate by II catalyst was also studied. The formation of ethyl but-2-enoate and ethyl-3-methylpent-2-enoate products was highly selective by 63 %. The unsaturated esters formation from the cross-metathesis degradation of natural rubber (99.9 % cis-polyisoprene) with dimethyl maleate and diethyl maleate using I-III catalysts was accomplished as well. I and II catalysts showed high activity in the degradation of natural rubber with diethyl maleate to produce the low molecular weight of oligomers unsaturated ester products (Mn = 1 x 103 g mol-1) with isoprene units of m = 10 – 27 and yields ranging from 68 to 94 %.

Scalable Synthesis of Functionalized Ferrocenyl Azides and Amines Enabled by Flow Chemistry

2019 ◽  
Author(s):  
Merlin Kleoff ◽  
Johannes Schwan ◽  
Lisa Boeser ◽  
Bence Hartmayer ◽  
Mathias Christmann ◽  
...  
Keyword(s):  
Reaction Time ◽  
Heterogeneous Reaction ◽  
Reduction Process ◽  
Flow Chemistry ◽  
Subsequent Reaction ◽  
Scalable Synthesis ◽  
High Yields ◽  
Reactor Section

A scalable access to functionalized 1,1’- and 1,2-ferrocenyl azides has been realized in flow. By halogen‒lithium exchange of ferrocenyl halides and subsequent reaction with tosyl azide, a variety of functionalized ferrocenyl azides was obtained in high yields. To allow a scalable preparation of these potentially explosive compounds, an efficient flow protocol was developed accelerating the reaction time to minutes and circumventing accumulation of potentially hazardous intermediates. Switching from homogeneous to triphasic flow amidst process was key for handling a heterogeneous reaction mixture formed after a heated reactor section. The corresponding and synthetically versatile ferrocenyl amines were then prepared by a reliable reduction process.

Endgroup and Sidechain Functionalization of Surface-Initiated ROMP Thin Films: Progress Towards ROMP-Based Molecular Wires

2018 ◽  
Author(s):  
Nicholas Marshall
Keyword(s):  
Thin Films ◽  
Contact Angle ◽  
Cyclic Voltammetry ◽  
Polymer Films ◽  
Conjugated Polymer ◽  
Ring Opening ◽  
Molecular Wires ◽  
Metathesis Polymerization ◽  
Cross Metathesis ◽  
Active Ester

A set of experiments in surface-initiated ring-opening metathesis polymerization, including end-functionalization of growing brushes and contact angle/cyclic voltammetry measurements. We report preparation and CV of two different conjugated polymer films, and several endgroup and sidechain functionalization experiments using cross-metathesis and active ester substitution.<br>

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