Catalytic alkynylation of ketones and aldehydes using quaternary ammonium hydroxide base

J Org Chem. 2003 May 2;68(9):3702-5. doi: 10.1021/jo026592g.


Catalytic alkynylation of diverse ketones and aldehydes using nonmetallic benzyltrimethylammonium hydroxide or a basic resin of the hydroxide type in DMSO is described. Aliphatic or alicyclic carbonyl partners gave satisfactory results, whereas aromatic ones afforded products with low yields. When aromatic aldehydes were reacted with phenylacetylene, enones such as chalcone derivatives were obtained in place of ynols. These organobase-catalyzed systems provide a practical nonmetallic protocol for C[bond]C formation.