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Basicity of Heterocyclic Aromatic Amines

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...

Criteria for Aromaticity and the Hückel 4n + 2 Rule

Criteria for Aromaticity and the Hückel 4n + 2 Rule

Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n + 2 rule.

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

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A general solution for the 2-pyridyl problem.

Graham R Dick¹, Eric M Woerly, Martin D Burke

¹Howard Hughes Medical Institute, Department of Chemistry, University of Illinois at Urbana-Champaign, 61801, USA.

Angewandte Chemie (International Ed. in English)

|January 31, 2012

Summary

This summary is machine-generated.

Researchers developed an air-stable 2-pyridyl borane for cross-coupling reactions. This breakthrough enables efficient synthesis with various aryl and heteroaryl halides, solving a long-standing challenge in organic chemistry.

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

Area of Science:

Organic Chemistry
Synthetic Chemistry
Catalysis

Background:

Air-stable 2-pyridyl boranes are crucial building blocks in organic synthesis.
Previous methods struggled with the instability and limited scope of 2-pyridyl boranes in cross-coupling reactions.
A general solution for effectively coupling these reagents with aryl and heteroaryl halides remained elusive.

Purpose of the Study:

To develop a general and efficient method for palladium-mediated cross-coupling using air-stable 2-pyridyl boronates.
To overcome the long-standing challenge of incorporating 2-pyridyl moieties into complex molecules.

Main Methods:

Palladium-catalyzed cross-coupling reactions.
Utilized a novel copper catalyst system, bis(diethanolamine)copper(II) [Cu(DEA)2], to enable the coupling.
Employed air-stable boronates as coupling partners with aryl and heteroaryl halides/pseudohalides.

Main Results:

Successfully demonstrated palladium-mediated cross-coupling of air-stable 2-pyridyl boronates.
Achieved effective coupling with a wide range of aryl and heteroaryl halides and pseudohalides.
The Cu(DEA)2 catalyst system proved powerful in enabling these challenging transformations.

Conclusions:

The discovery provides a general and robust solution for synthesizing compounds containing the 2-pyridyl group.
This advancement significantly expands the synthetic utility of 2-pyridyl boronates in organic chemistry.
The developed method offers a practical approach for accessing diverse molecular architectures.