Palladium-Catalyzed Thiocarbonylations with TIPS Thioethers

Synlett ◽  
2022 ◽  
Author(s):  
Yosuke Hosoya ◽  
Kota Mizoguchi ◽  
Honoka Yasukochi ◽  
Masahisa Nakada
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalyzed ◽  
High Yields

Herein, we describe a palladium-catalyzed thiocarbonylation via the reaction of a σ-alkyl palladium intermediate with carbon monoxide (CO) and a TIPS thioether. The use of CsF, (IPr)Pd(allyl)Cl, CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depends on the structure of substrate and it was observed that indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with PhSTIPS and CsF were also demonstrated to form the corresponding thioesters.

Iodide-Catalyzed Carbonylation–Benzylation of Benzyl Chlorides with Potassium Aryltrifluoroborates under Ambient Pressure of Carbon Monoxide

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 369-374 ◽  
Author(s):  
Wei Han ◽  
Junjie Chen ◽  
Fengli Jin ◽  
Xiaorong Yuan
Keyword(s):  
Carbon Monoxide ◽  
Ambient Pressure ◽  
The Novel ◽  
Metal Free ◽  
Benzyl Chlorides ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Novel Method ◽  
High Yields ◽  
Co Gas

Tetra-N-butylammonium iodide (TBAI) catalyzed carbonylation–benzylation of unactivated benzyl chlorides with potassium aryltrifluoroborates using CO gas has been developed. This reaction is transition-metal free, is carried out under ambient pressure, and provides a wide range of 1,2,3-triarylpropan-1-one derivatives in high yields. The novel method represents a significant improvement over the traditional palladium-catalyzed carbonylation.

Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones

Synthesis ◽  
2019 ◽  
Vol 52 (04) ◽  
pp. 581-590 ◽  
Author(s):  
Zhaotao Xu ◽  
Bin Huang ◽  
Zebiao Zhou ◽  
Mingzhong Cai
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalyst ◽  
Functional Group ◽  
Atom Economy ◽  
Highly Efficient ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
High Yields

A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N,N-diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

Palladium-catalyzed carbonylation of 1,5-cyclooctadiene. Effects of temperature and pressure

1991 ◽  
Vol 56 (3) ◽  
pp. 663-672 ◽  
Author(s):  
Curtis B. Anderson ◽  
Rade Marković
Keyword(s):  
Carbon Monoxide ◽  
Oxidative Carbonylation ◽  
Influence Of Temperature ◽  
Carbonylation Reaction ◽  
Palladium Catalyzed ◽  
Effects Of Temperature ◽  
Temperature And Pressure

The influence of temperature and carbon monoxide pressure on the course of oxidative carbonylation reaction of 1,5-cyclooctadiene in the presence of the palladium(II) salts as a catalyst, was investigated.

Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zheng-Yang Gu ◽  
Yang Wu ◽  
Feng Jin ◽  
Bao Xiaoguang ◽  
Ji-Bao Xia
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalysis ◽  
Computational Studies ◽  
Organic Azides ◽  
Reaction Proceeds ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
And Control

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

Design and use of an Efficient Plasma Jet Reactor for High Temperature Gas/Solid Reactions

1983 ◽  
Vol 30 ◽  
Author(s):  
F. W. Giacobbe ◽  
D. W. Schmerling
Keyword(s):  
Carbon Monoxide ◽  
High Temperature ◽  
Arc Discharge ◽  
Plasma Jet ◽  
Direct Result ◽  
Discharge Region ◽  
Plasma Flame ◽  
Powdered Carbon ◽  
High Yields ◽  
Experimental Trials

ABSTRACTA unique and efficient plasma jet reactor has been developed and used to study the high temperature production of carbon monoxide from a reaction between powdered carbon and a pure carbon dioxide plasma. The plasma jet reactor was designed to allow the injection of powdered carbon above the arc discharge region rather than into the plasma flame below the arc discharge region. High yields of carbon monoxide, produced at relatively high efficiencies, were a direct result of this technique. The plasma jet was also designed to enable rapid changing and testing of various anode insertsAverage yields of carbon monoxide in the product gases were as high as 80–87% in selected experimental trials. Carbon monoxide was produced at rates exceeding 15,000 1/hr (at STP) with a power expenditure of 52 Kw.

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