Draft:Propargylation

Propargylation is an addition reaction that adds a propargyl group (−CH2C≡CH) to an organic compound. Due to the diversity of both reagents compatible with propargylation and reactions of the alkyne product, it has been called one of the most important tools in organic synthesis.[1]

History

Prior to the 21st century, the primary propargylation reaction was the Nicolas reaction,[2] which uses a Lewis acid and dicobalt octacarbonyl to produce a propargylic carbocation complex, stabilised by delocalisation of charge onto cobalt. The cationic carbon is then attacked by a nucleophile, and oxidation removes the cobalt moiety and regenerates the alkyne.

Allenyl tautomerism

The propargyl and allenyl radicals exhibit significant tautomerism, with the radical electron delocalised across the terminal and propargylic carbon.[3] This allows both propargyl and allenyl compounds to be reagents in propargylation, but also means propargylation processes must be engineered for selectivity of the propargylic product.

Sources

  1. ^ Ding, Chang-Hua; Hou, Xue-Long (2011). "Catalytic Asymmetric Propargylation". Chemical Reviews. 111 (3): 1914–1937. doi:10.1021/cr100284m. PMID 21344874.
  2. ^ Roy, Rashmi; Saha, Satyajit (2018). "Scope and advances in the catalytic propargylic substitution reaction". RSC Advances. 8 (54): 31129–31193. doi:10.1039/c8ra04481c. PMC 9085608. PMID 35548716.
  3. ^ Xiao, Bi-Yin; Huang, Wei; Zhang, Feng-Hua (2025). "Recent Advances in the Formation and Transformation of Propargyl Radical". European Journal of Organic Chemistry. 28 (25) e202500302. doi:10.1002/ejoc.202500302.

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