141821-06-9Relevant articles and documents
Room Temperature Allenation of Terminal Alkynes with Aldehydes
Cui, Yifan,Li, Can,Ma, Shengming,Xiao, Junzhe,Xu, Haibo,Zhai, Yizhan,Zhang, Xue
supporting information, p. 25708 - 25713 (2021/11/09)
A gold-catalyzed room temperature allenation of terminal alkynes (ATA) with aldehydes affording 1,3-disubstituted allenes with diverse functional groups has been developed by identifying a gold(I) catalyst and an amine. The practicality of this reaction has been demonstrated by a ten gram-scale synthesis and the synthetic potentials have been demonstrated via various transformations and formal total synthesis of (?)-centrolobine. Mechanistic studies revealed that the gold catalyst, the aldehyde effect, the fluoroalkyl hydroxyl solvent (TFE or HFIP) and the structure of amine are vital in this room temperature ATA reaction.