22965-93-1Relevant academic research and scientific papers
Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process
Du, Chan,Fang, Jianghua,Fang, Yewen,Lei, Wan,Li, Yan,Liu, Yongjun
, p. 8502 - 8506 (2021/10/20)
Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.
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
supporting information, p. 1417 - 1420 (2016/05/19)
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.
α-Haloenones from secondary alkynols
Angara,McNelis
, p. 2099 - 2100 (2007/10/02)
α-Iodoenones and α-bromoenones are formed from secondary alkynols by the use of the appropriate N-halosuccinimide and a catalytic amount of certain Lewis acids. For example, 3-hexyn-2-ol (1) was converted to (Z)-4-iodo-4-hexen-3-one (2) in 85-95% yields w
