Related Experiment Video
Updated: Sep 27, 2025
08:56
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
2.9K
Copper-free Sonogashira cross-coupling reactions: an overview
Fatemeh Mohajer1, Majid M Heravi1, Vahideh Zadsirjan1
1Department of Physics and Chemistry, School of Science, Alzahra University PO Box 1993891176, Vanak Tehran Iran mmh1331@yahoo.com mmheravi@alzahra.ac.ir +98 21 88041344 +98 21 88044051.
RSC Advances
|April 15, 2022
Summary
The Sonogashira reaction, a vital C-C bond formation method, can now be performed without copper co-catalysts or amine bases. This advancement supports green chemistry and economic viability in organic synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Green Chemistry
Background:
- The Sonogashira reaction is a palladium-catalyzed cross-coupling reaction forming C-C bonds between vinyl/aryl halides and terminal alkynes.
- Traditionally requires copper co-catalysts and phosphine/amine bases, operating under mild conditions.
- Widely applied in synthesizing pharmaceuticals, natural products, nanomaterials, and complex organic molecules.
Purpose of the Study:
- To review recent developments in Sonogashira reactions performed without copper co-catalysts.
- To highlight advancements in Sonogashira reactions conducted without phosphine or amine bases.
- To discuss the implications for green chemistry and economic feasibility.
Main Methods:
- Focuses on critical review of literature concerning copper-free Sonogashira reactions.
- Examines methodologies that eliminate the need for phosphine or amine bases.
- Analyzes the efficiency and scope of these modified Sonogashira protocols.
Main Results:
- Demonstrates successful Sonogashira reactions without copper co-catalysts.
- Highlights successful Sonogashira reactions without phosphine or amine bases.
- Identifies specific conditions and catalysts enabling these copper-free and base-free transformations.
Conclusions:
- Sonogashira reactions can be effectively performed without traditional copper co-catalysts and amine bases.
- These advancements align with green chemistry principles by reducing hazardous reagents.
- Eliminating copper and amine bases offers economic advantages and simplifies reaction procedures.
More Related Videos
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
Related Concept Videos
01:04Crossed Aldol Reactions: Overview
5.6K
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
5.6K
01:16Cycloaddition Reactions: Overview
2.9K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.9K
01:26Limitations of Friedel–Crafts Reactions
5.8K
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
5.8K
01:14Phase II Conjugation Reactions: Overview
380
Conjugation, a key component of phase II biotransformation reactions, is a vital process in drug detoxification. It involves transferring endogenous substances like glucuronic acid, sulfate, and glycine to drugs or their metabolites formed in phase I reactions. These conjugation reactions, often catalyzed by specific enzymes, transform potentially harmful metabolites into inactive, water-soluble forms easily excreted in urine or bile. By enhancing polarity and eliminating pharmacological...
380
01:19Phase II Reactions: Miscellaneous Conjugation Reactions
132
Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...
132
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K