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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Pericyclic Reactions: Introduction01:17

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Nickel-Catalyzed Ligand-Controlled Selective Reductive Cyclization/Cross-Couplings.

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Nickel-catalyzed reductive difunctionalization of alkenes offers a robust method for creating chiral heterocycles with quaternary stereocenters. This strategy provides a versatile alternative to traditional methods, enabling diverse synthetic applications.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Quaternary stereocenters are crucial for optimizing drug candidates due to improved physicochemical and pharmacokinetic properties.
  • Palladium-catalyzed methods for constructing quaternary stereocenters via alkene difunctionalization face limitations in chemoselectivity, air sensitivity, and precursor accessibility.
  • Nickel-catalyzed reductive cross-coupling is a powerful tool for C(sp³)-C bond formation, but enantioselective coupling of C(sp³) electrophiles often requires unstable precursors.

Purpose of the Study:

  • To develop and summarize Ni-catalyzed reductive difunctionalization of alkenes via selective cyclization/cross-coupling as a robust and practical alternative.
  • To explore the modulation of enantioselectivity and cyclization modes in reductive cyclization/cross-couplings.
  • To provide strategic complementarity for existing reductive cross-coupling methods and enable the synthesis of valuable chiral heterocycles with quaternary stereocenters.

Main Methods:

  • Investigated Ni-catalyzed enantioselective reductive cyclization/cross-coupling using various ligands, reductants, and additives.
  • Explored a wide range of electrophiles including aryl halides, vinyl halides, alkynyl halides, gem-difluoroalkenes, CO₂, trifluoromethyl alkenes, and cyano electrophiles.
  • Tuned catalyst steric effects using modified bipyridine ligands to control regiodivergent cyclization/cross-couplings (exo- vs. endo-selective) and enable amide substrate activation.

Main Results:

  • Successfully constructed valuable chiral heterocycles with quaternary stereocenters using Ni-catalyzed reductive cyclization/cross-coupling.
  • Demonstrated tunable selectivity (exo/endo) by modifying bipyridine ligands, enabling divergent synthesis of pharmacologically important 2-benzazepine frameworks.
  • Discovered a switchable skeletal rearrangement strategy by altering ligand properties and nickel oxidation states, offering a novel approach to C-C bond activation.

Conclusions:

  • Ni-catalyzed reductive difunctionalization of alkenes provides a versatile and practical approach to synthesize chiral heterocycles with quaternary stereocenters.
  • Ligand design is critical for controlling enantioselectivity, cyclization modes, and enabling skeletal rearrangements.
  • The developed methods offer strategic complementarity and expand the scope of C(sp³)-C bond formation, with demonstrated potential in synthesizing biologically relevant molecules.