Reactions of alkynes with C-S bond formation: recent developments

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Sulfur Chemistry

Background:

• Alkynes are fundamental building blocks in organic synthesis.
• The formation of carbon-sulfur (C-S) bonds is crucial for synthesizing various organic molecules.
• Recent advancements have expanded the scope of alkyne functionalization with sulfur-containing moieties.

Purpose of the Study:

• To provide a comprehensive overview of recent (2013-2023) advances in alkyne C-S bond formation.
• To systematically discuss reactions involving alkynes and a wide array of sulfur reagents.
• To elucidate the diverse reaction mechanisms and substrate scopes in alkyne-sulfur chemistry.

Main Methods:

• Literature review of scientific publications from 2013 to 2023.
• Categorization of reactions based on alkyne substrates and sulfur reagent types.
• Analysis of reaction mechanisms, including radical, electrophilic/nucleophilic addition, and copper-catalyzed azide-alkyne cycloaddition (CuAAC).

Main Results:

• Detailed discussion of reactions between alkynes and over 30 distinct sulfur-containing reagents (e.g., disulfides, thiols, elemental sulfur, sulfonyl chlorides).
• Exploration of various reaction pathways, highlighting their mechanistic intricacies.
• Organization of findings by substrate and reactivity patterns for clarity.

Conclusions:

• Significant progress has been made in alkyne C-S bond formation over the past decade.
• The reviewed reactions offer versatile strategies for incorporating sulfur into organic frameworks.
• This review serves as a valuable resource for researchers exploring novel alkyne functionalizations and sulfur chemistry.