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One-Pot Synthesis of 1,3-Disubstituted Allenes from 1-Alkynes, Aldehydes, and Morpholine

Jinqiang Kuang and Shengming Ma*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China, Email:

J. Kuang, S. Ma, J. Am. Chem. Soc., 2010, 132, 1786-1787.

DOI: 10.1021/ja910503k

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ZnI2 is a catalyst for a one-step synthesis of allenes from terminal alkynes and both aromatic and aliphatic aldehydes with morpholine as the base in toluene. The reaction proceeds via propargylic amines, which were converted to allenes by a sequential hydride transfer and β-elimination process. Functionalities such as halide, hydroxyl, or amine are tolerated.

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Catalytic Asymmetric Synthesis of Optically Active Allenes from Terminal Alkynes

J. Ye, S. Li, B. Chen, W. Fan, J. Kuang, J. Liu, Y. Liu, B. Miao, B. Wan, Y. Wang, X. Xie, Q. Yu, W. Yuan, S. Ma, Org. Lett., 2012, 14, 1346-1349.

An Efficient Synthesis of Terminal Allenes from Terminal 1-Alkynes

J. Kuang, S. Ma, J. Org. Chem., 2009, 74, 1763-1765.

Key Words


ID: J48-Y2010-0430