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Phase II Reactions: Methylation Reactions01:17

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Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
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Late-stage difluoromethylation: concepts, developments and perspective.

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Recent advances in difluoromethylation enable the formation of crucial X-CF2H bonds. New reagents and methods streamline access to pharmaceutical compounds, driving interest in process chemistry.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Difluoromethylation is vital for synthesizing molecules with pharmaceutical relevance.
  • Traditional methods for X-CF2H bond formation have limitations.

Purpose of the Study:

  • To review recent advances in difluoromethylation processes.
  • To highlight novel reagents and methodologies for X-CF2H bond formation.

Main Methods:

  • Metal-based methods for C(sp2) difluoromethylation (stoichiometric and catalytic).
  • Minisci-type radical chemistry for C(sp2)-H difluoromethylation.
  • Electrophilic, nucleophilic, radical, and cross-coupling methods for C(sp3)-CF2H bonds.
  • Novel non-ozone depleting difluorocarbene reagents for X-H insertion (X=O, N, S).

Main Results:

  • Significant progress in metal-catalyzed difluoromethylation of C(sp2) sites.
  • Development of radical and cross-coupling strategies for C(sp3) difluoromethylation.
  • Emergence of site-selective difluoromethylation, including on biomolecules.
  • Introduction of new reagents for X-H difluoromethylation, replacing ozone-depleting substances.

Conclusions:

  • Recent advances have significantly improved access to difluoromethylated compounds.
  • Novel methods offer efficient and selective difluoromethylation strategies.
  • These developments are crucial for pharmaceutical synthesis and process chemistry.