One-pot synthesis of 1,3-disubstituted allenes from 1-alkynes, aldehydes, and morpholine.
ZnI(2) has been identified as the catalyst for the one-step synthesis of allenes from terminal alkynes and aldehydes with morpholine as the base in toluene. The reaction is believed to proceed via the intermediacy of propargylic amines, which was converted to allenes by a sequential hydride transfer and beta-elimination process. The reaction is applicable for both aromatic and aliphatic aldehydes. Functionalities such as halide, hydroxyl, or amine may be tolerated.
Kuang
Jinqiang
J
Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, PR China.
Ma
Shengming
S
D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D007454:Iodides / Q000737:chemistry; D009025:Morpholines / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry
D000447:Aldehydes; D000466:Alkadienes; D000480:Alkynes; D007454:Iodides; D009025:Morpholines; D017967:Zinc Compounds; C025947:propadiene; C029770:zinc iodide; C037574:morpholine