32147-17-4Relevant academic research and scientific papers
Direct Conversion of Internal Alkynes into α-Iodoenones: One-Step Collaborative Iodination and Oxidation
Wang, Youliang,Genoux, Alexandre,Ghorai, Subir,Chen, Hongyi,Todd, Robert,Zhang, Liming
, p. 1417 - 1420 (2016)
The reaction of an internal alkyne with 2,6-dichloropyridine N-oxide, a nucleophilic oxidant, and electrophilic N-iodosuccinimide (NIS) simultaneously enables the direct access to versatile α-iodoenones. Electronically biased internal alkynes undergo the one-step transformation with excellent regioselectivities and with practical Z/E ratios. In comparison to the related oxidative gold catalysis using pyridine N-oxides, this reaction employs NIS as the stoichiometric ynophile instead of the soft acidic noble metal catalyst and affords products featuring an additional versatile C-I bond. Similar strategies for replacing ynophilic cationic gold(I) complexes in oxidative gold catalysis with likewise ynophilic stoichiometric electrophiles would enable the development of new synthetic methods.
