CO Surrogates: A Green Alternative in Palladium-Catalyzed CO Gas Free Carbonylation Reactions

2020 ◽  
Vol 24 (22) ◽  
pp. 2588-2600
Author(s):  
Mayur V. Khedkar ◽  
Shoeb R. Khan ◽  
Trimurti L. Lambat ◽  
Ratiram G. Chaudhary ◽  
Ahmed A. Abdala
Keyword(s):  
Carbon Monoxide ◽  
Fine Chemicals ◽  
Large Excess ◽  
Specific Reaction ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Direct Use ◽  
Substantial Interest ◽  
Co Gas

Carbonylation reactions with carbon monoxide (CO) provide efficient and attractive routes for the synthesis of bulk and fine chemicals. However, the practice of using a large excess of an inflammable, lethal and greenhouse CO gas is always a concern in this chemistry. The development of CO surrogates has gained substantial interest and become a green alternative to gaseous CO. Many of the recent studies have focused on the development of other benign and safe reagents to work as a CO source in carbonylation reactions, and the assortment of feasible CO surrogates for specific reaction can be accomplished by the literature data. This review describes the recent developments in palladium-catalyzed carbonyl insertions without the direct use of gaseous CO.

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.

Palladium-Catalyzed Carbonylation of Coumarin C(sp2)–H Bonds: A New Entry to Arylcoumarin Ketones

Synthesis ◽  
2018 ◽  
Vol 51 (07) ◽  
pp. 1680-1688 ◽  
Author(s):  
Rahim Pashazadeh ◽  
Siyavash Mirzaei ◽  
Saideh Rajai-Daryasarei ◽  
Mehdi Soheilizad ◽  
Roya Kabiri ◽  
...  
Keyword(s):  
Carbon Monoxide ◽  
Aryl Halides ◽  
Reaction Conditions ◽  
Oxidative Functionalization ◽  
Palladium Catalyzed ◽  
Co Gas ◽  
New Entry

A facile and efficient palladium-catalyzed carbonylation of coumarins involving two C–C bond formations has been developed. The C–H bond oxidative functionalization proceeds through aroylation with insertion of carbon monoxide to give arylcoumarin ketones. The reaction conditions, employing ambient pressures of CO gas as C1 feedstock, dramatically improve the generality of the carbonylation of aryl halides.

A new route to carbon monoxide adducts of heme proteins

2008 ◽  
Vol 12 (10) ◽  
pp. 1096-1099 ◽  
Author(s):  
Sergei V. Makarov ◽  
Denis S. Salnikov ◽  
Anna S. Pogorelova ◽  
Zoltan Kis ◽  
Radu Silaghi-Dumitrescu
Keyword(s):  
Carbon Monoxide ◽  
Cytochrome C ◽  
Heme Proteins ◽  
Single Step ◽  
Anaerobic Conditions ◽  
Large Excess ◽  
Thiourea Dioxide ◽  
Hydrolysis Of ◽  
Protein Moiety ◽  
Co Gas

Sulfoxylate SO 2 H −( SO 22−), a strong reducing agent readily produced by hydrolysis of thiourea dioxide, reacts with ferric myoglobin ( Mb ) to reversibly produce Fe (II)- Mb , starting from either aerobic or anaerobic conditions. Exposure of Fe (II)- Mb to excess sulfoxylate further produces Fe (II)- CO - Mb . Fe (II)- Mb can be regenerated by reoxidation with ferricyanide at this stage; hemin, rubredoxin and cytochrome c show a similar reactivity towards sulfoxylate. The source of CO is not the protein moiety, nor is it the heme or the thiourea dioxide – but rather CO 2, via its reaction with sulfoxylate when the latter is used in large excess. These findings provide a convenient single-step route to carbon monoxide heme adducts, without the need to manipulate toxic CO gas.

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.

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

Synthesis ◽  
2020 ◽  
Author(s):  
Lili Shi ◽  
Junkai Fu ◽  
Shuangqiu Gao ◽  
Le Chang ◽  
Binglin Wang
Keyword(s):  
Heck Reaction ◽  
Alkyl Radicals ◽  
Type Reaction ◽  
The Past ◽  
Alkyl Electrophiles ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Initial Work ◽  
Activated Olefins ◽  
Pseudo Halides

AbstractThe Mizoroki–Heck reaction is considered as one of the most ingenious and widely used methods for constructing C–C bonds. This reaction mainly focuses on activated olefins (styrenes, acrylates, or vinyl ethers) and aryl/vinyl (pseudo) halides. In comparison, the studies on unactivated alkenes and alkyl electrophiles are far less due to the low reactivity, poor selectivity, as well as competitive β-H elimination. In the past years, a growing interest has thus been devoted and significant breakthroughs have been achieved in the employment of unactivated alkenes and alkyl electrophiles as the reaction components, and this type of coupling is called as Heck-type or Heck-like reaction, which distinguishes from the traditional Heck reaction. Herein, we give a brief summary on Heck-type reaction between unactivated alkenes and alkyl electrophlies, covering its initial work, recent advancements, and mechanistic discussions.1 Introduction2 Intramolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles2.1 Cobalt-Catalyzed Intramolecular Heck-Type Reaction2.2 Palladium-Catalyzed Intramolecular Heck-Type Reaction2.3 Nickel-Catalyzed Intramolecular Heck-Type Reaction2.4 Photocatalysis and Multimetallic Protocol for Intramolecular Heck-Type Reaction3 Intermolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles3.1 Electrophilic Trifluoromethylating Reagent as Reaction Partners3.2 Alkyl Electrophiles as Reaction Partners4 Oxidative Heck-Type Reaction of Unactivated Alkenes and Alkyl Radicals5 Conclusions and Outlook

scholarly journals Nitrile Synthesis with Aldoxime Dehydratases: A Biocatalytic Platform with Applications in Asymmetric Synthesis, Bulk Chemicals, and Biorefineries

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4466
Author(s):  
Pablo Domínguez de María
Keyword(s):  
Asymmetric Synthesis ◽  
Organic Solvents ◽  
Raw Materials ◽  
Aqueous Media ◽  
Industrial Processes ◽  
Polymer Chemistry ◽  
Fine Chemicals ◽  
Mild Conditions ◽  
Bulk Chemicals ◽  
Recent Developments

Nitriles comprise a broad group of chemicals that are currently being industrially produced and used in fine chemicals and pharmaceuticals, as well as in bulk applications, polymer chemistry, solvents, etc. Aldoxime dehydratases catalyze the cyanide-free synthesis of nitriles starting from aldoximes under mild conditions, holding potential to become sustainable alternatives for industrial processes. Different aldoxime dehydratases accept a broad range of aldoximes with impressive high substrate loadings of up to >1 Kg L−1 and can efficiently catalyze the reaction in aqueous media as well as in non-aqueous systems, such as organic solvents and solvent-free (neat substrates). This paper provides an overview of the recent developments in this field with emphasis on strategies that may be of relevance for industry and sustainability. When possible, potential links to biorefineries and to the use of biogenic raw materials are discussed.

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.

Photoactive conjugated polymer/graphdiyne nanocatalyst for CO2 reduce into CO in living cells for hypoxia tumor treatment

2021 ◽  
Author(s):  
Endong Zhang ◽  
Zicheng Zuo ◽  
Wen Yu ◽  
Hao Zhao ◽  
Shengpeng Xia ◽  
...  
Keyword(s):  
Carbon Monoxide ◽  
Photodynamic Therapy ◽  
Tumor Microenvironment ◽  
Conjugated Polymer ◽  
Tumor Therapy ◽  
Living Cells ◽  
Tumor Treatment ◽  
Treatment Efficiency ◽  
Therapy Strategy ◽  
Co Gas

Carbon monoxide (CO) gas therapy has grown to be an emerging tumor therapy strategy to avoid low treatment efficiency of photodynamic therapy (PDT) caused by the hypoxia tumor microenvironment. However,...

scholarly journals Adapting decarbonylation chemistry for the development of prodrugs capable of in-vivo delivery of carbon monoxide utilizing sweeteners as carrier molecules

2021 ◽  
Author(s):  
Ladie Kimberly De La Cruz ◽  
Xiaoxiao Yang ◽  
Anna Menshikh ◽  
Maya Brewer ◽  
Wen Lu ◽  
...  
Keyword(s):  
Carbon Monoxide ◽  
Animal Models ◽  
Therapeutic Agent ◽  
Organ Injury ◽  
Signaling Molecule ◽  
In Vivo Delivery ◽  
Co Gas

Carbon monoxide as an endogenous signaling molecule exhibits pharmacological efficacy in various animal models of organ injury. To address the difficulty in using CO gas as a therapeutic agent for...

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