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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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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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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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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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Properties of Organometallic Compounds01:23

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Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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Limitations of Friedel–Crafts Reactions01:26

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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...
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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Merging Multicomponent Reactions and Metal-Free C-H Functionalization: Emerging Tools in Organic Synthesis.

Ariful Islam1, B Shriya Saikia1, Pranjal K Baruah2

  • 1Department of Applied Sciences, GUIST, Gauhati University, Guwahati, Assam, 781014, India.

Topics in Current Chemistry (Cham)
|December 13, 2025
PubMed
Summary

Metal-free multicomponent reactions (MCRs) using C-H functionalization offer sustainable synthesis of complex heterocycles. This review covers advances in metal-free MCRs for efficient, green construction of bioactive molecules.

Keywords:
C–H functionalizationGreen chemistryHeterocyclic chemistryMetal-freeMulticomponent reaction

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Synthetic Methodology

Background:

  • Metal-free multicomponent reactions (MCRs) are crucial for sustainable and atom-economical organic synthesis.
  • Direct C-H bond functionalization offers a powerful strategy for efficient molecular construction.
  • Developing metal-free approaches is essential for reducing environmental impact and cost in synthesis.

Purpose of the Study:

  • To review recent advances (2016-2025) in metal-free C-H functionalization strategies integrated with MCRs.
  • To highlight the efficient construction of complex, bioactive heterocycles using these methods.
  • To analyze the mechanistic platforms, scope, selectivity, and green metrics of these reactions.

Main Methods:

  • Exploration of mechanistic platforms including iminium ion activation, azomethine ylide chemistry, radical-mediated transformations, visible-light photoredox catalysis, and base-mediated protocols.
  • Critical analysis of substrate scope, regioselectivity, stereoselectivity, and practical applicability.
  • Evaluation of green metrics and alignment with green chemistry principles.

Main Results:

  • Demonstration of diverse metal-free MCRs for constructing complex heterocyclic scaffolds.
  • Identification of key mechanistic pathways enabling efficient C-H functionalization within MCRs.
  • Highlighting the use of renewable feedstocks, solvent-free conditions, and recyclable catalysts.

Conclusions:

  • Metal-free MCRs via C-H functionalization represent a significant advancement in sustainable organic synthesis.
  • These methodologies provide efficient access to structurally diverse heterocyclic compounds for pharmaceutical and materials science.
  • The field shows strong alignment with green chemistry principles, offering practical and environmentally friendly synthetic solutions.