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Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
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Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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A permanent electric dipole orients itself along an external electric field. This rotation can be quantified by defining the potential energy because the external torque does work in rotating it. Then, the potential energy is minimum at the parallel configuration and maximum at the antiparallel configuration. While the former is a stable equilibrium, the latter is an unstable equilibrium.
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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Materials consisting of paired electrons have zero net magnetic moments. However, when these materials are placed under an external magnetic field, the moments opposite to the field are induced. Such materials are called diamagnets. Diamagnetism is the response of the diamagnets when placed in an external magnetic field.
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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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High-order dipolar annulations with metal-containing reactive dipoles.

Mao-Mao Zhang1, Bao-Le Qu1, Bin Shi1

  • 1CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, China. luliangqiu@mail.ccnu.edu.cn.

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Metal-catalyzed dipolar annulations offer an efficient route to medium-sized heterocycles. Asymmetric catalysis enables the selective synthesis of chiral heterocycles, crucial for pharmaceuticals.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Medium-sized heterocycles are vital scaffolds in natural products and pharmaceuticals.
  • Traditional methods for heterocycle synthesis often lack efficiency and flexibility.
  • Metal-catalyzed reactions provide powerful tools for complex molecule construction.

Purpose of the Study:

  • To review advances in metal-catalyzed high-order dipolar annulations for heterocycle synthesis.
  • To highlight the mechanistic differences between these reactions and pericyclic reactions.
  • To showcase the application of asymmetric catalysis in creating chiral heterocycles.

Main Methods:

  • Focus on metal-catalyzed high-order dipolar annulation reactions.
  • Discussion of stepwise reaction pathways distinct from pericyclic mechanisms.
  • Emphasis on the use of chiral organometallic catalysts for asymmetric synthesis.

Main Results:

  • Metal-catalyzed dipolar annulations are efficient and flexible strategies.
  • These reactions proceed via stepwise pathways, not Woodward-Hoffman rules.
  • Asymmetric annulations yield chiral heterocycles with high selectivity.

Conclusions:

  • High-order dipolar annulations are key for synthesizing medium-sized heterocycles.
  • Asymmetric variants are crucial for enantioselective and diastereoselective synthesis.
  • This methodology offers significant potential in drug discovery and development.