Beyond Acetylene: Exploring Solvent Stabilization of Calcium Carbide‐derived Acetylide Intermediates and Their Significance in Small Organic Molecule Synthesis

Hainer, Andrew S.; Lanterna, Anabel E.; Scaiano, Juan C.

Abstract

The reaction of calcium carbide with water has been widely used as a source of acetylene for the synthesis of organic molecules. In contrast with this traditional approach, we use the CaC2 reaction under water-starved conditions and show reactions that involve a calcium acetylide intermediate, reminiscent of Grignard reaction intermediates, which are stabilized by the solvent. Using this reaction pathway may allow for new chemistry, finer reaction control, and safety by limiting the formation of acetylene gas during the reaction. For example, reaction with bromoarenes, readily yields the corresponding diaryl acetylene.

Citation

Hainer, A. S., Lanterna, A. E., & Scaiano, J. C. (2024). Beyond Acetylene: Exploring Solvent Stabilization of Calcium Carbide‐derived Acetylide Intermediates and Their Significance in Small Organic Molecule Synthesis. ChemistrySelect, 9(14), Article e202400501. https://doi.org/10.1002/slct.202400501

• Journal Article Type: Article
• Acceptance Date: Mar 8, 2024
• Online Publication Date: Apr 4, 2024
• Publication Date: Apr 12, 2024
• Deposit Date: Apr 8, 2024
• Publicly Available Date: Apr 9, 2024
• Journal: ChemistrySelect
• Electronic ISSN: 2365-6549
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 9
• Issue: 14
• Article Number: e202400501
• DOI: https://doi.org/10.1002/slct.202400501
• Keywords: Palladium catalysis; Acetylide intermediate; Catalysis and Calcium carbide
• Public URL: https://nottingham-repository.worktribe.com/output/33294156
• Publisher URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.202400501