Room Temperature Allenation of Terminal Alkynes with Aldehydes

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  • Junzhe Xiao
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
  • Yifan Cui
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
  • Can Li
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
  • Haibo Xu
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
  • Yizhan Zhai
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
  • Xue Zhang
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
  • Shengming Ma
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China

Abstract

<jats:title>Abstract</jats:title><jats:p>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.</jats:p>

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