![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Anthranilamide (aam)-substituted diboron: palladium-catalyzed selective B(aam) transfer
Shintaro Kamio1, Ikuo Kageyuki, Itaru Osaka
1Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan. yhiroto@hiroshima-u.ac.jp.
Chemical Communications (Cambridge, England)
|August 4, 2018
Summary
Researchers synthesized an unsymmetrical diboron compound with an anthranilamide (aam) group. This compound selectively couples with aryl halides via a palladium-catalyzed reaction, forming diverse aryl-boryl products.
Area of Science:
- Organoboron chemistry
- Organic synthesis
- Catalysis
Background:
- Unsymmetrical diboron compounds are valuable synthetic intermediates.
- Palladium-catalyzed cross-coupling reactions are essential tools in organic synthesis.
- Miyaura-Ishiyama-type reactions enable the formation of carbon-boron bonds.
Purpose of the Study:
- To synthesize a novel unsymmetrical diboron reagent bearing an anthranilamide (aam) substituent.
- To investigate the reactivity of this new diboron compound in palladium-catalyzed cross-coupling reactions.
- To achieve selective borylation of aryl halides.
Main Methods:
- Synthesis of the unsymmetrical diboron reagent.
- Palladium-catalyzed Miyaura-Ishiyama-type coupling reaction with various aryl halides.
- Characterization of the resulting borylated products.
Main Results:
- Successful synthesis of the anthranilamide-substituted unsymmetrical diboron.
- The diboron compound selectively transferred the aam-substituted boryl moiety.
- Exclusive formation of diverse aryl-boryl(aam) compounds (Ar-B(aam)) was achieved.
- High yields and selectivity were observed in the coupling reactions.
Conclusions:
- The novel anthranilamide-substituted diboron is a versatile reagent for selective borylation.
- The palladium-catalyzed Miyaura-Ishiyama-type reaction provides an efficient route to Ar-B(aam) compounds.
- This methodology expands the scope of organoboron synthesis and offers access to valuable synthetic intermediates.
Related Concept Videos
02:36Transfer RNA Synthesis
13.4K
One of the unique features of tRNA is the presence of modified bases. In some tRNAs, modified bases account for nearly 20% of the total bases in the molecule. Altogether, these unusual bases protect the tRNA from enzymatic degradation by RNases.
Each of these chemical modifications is carried by a specific enzyme, post-transcription. All of these enzymes have unique base and site-specificity. Methylation, the most common chemical modification, is carried by at least nine different enzymes, with...
Each of these chemical modifications is carried by a specific enzyme, post-transcription. All of these enzymes have unique base and site-specificity. Methylation, the most common chemical modification, is carried by at least nine different enzymes, with...
13.4K
01:23Trigonometric Substitution
73
Trigonometric substitution is a technique used to simplify integrals that contain square root expressions involving quadratic forms. It is particularly effective when the integrand includes terms resembling those found in standard geometric equations, such as circles or ellipses.Molniya satellites follow highly elliptical orbits, repeatedly sweeping out the same regions of space as they revolve around Earth. To estimate the area enclosed by such an orbit, the path is modeled as an ellipse...
73
01:29Rationalizing Substitutions
62
Integrals involving non-rational functions are often difficult to evaluate using standard techniques, especially when radicals appear in the integrand. Rationalizing substitution provides a systematic method for simplifying such integrals by converting them into rational forms that are easier to handle.Consider a rod whose linear mass density depends on a constant linear density, a characteristic length, and the distance from the left end of the rod. Determining the total mass requires...
62
02:24Acid-Catalyzed Ring-Opening of Epoxides
9.0K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
9.0K
02:26Base-Catalyzed Ring-Opening of Epoxides
10.2K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
10.2K
01:32What is Natural Selection?
129.6K
Natural selection is an evolutionary process in which individuals with survival-promoting traits reproduce at higher rates. These favorable traits become more common within a population or species. Naturally selected traits initially arise via random genetic mutations. In order for selection to occur, there must be variation within a population, the trait controlling the variation must be heritable, and there must be an evolutionary advantage for variation in the trait.
129.6K