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Mild-Condition Synthesis of Allenes from Alkynes and Aldehydes Mediated by Tetrahydroisoquinoline (THIQ)

Guo-Jie Jiang, Qin-Heng Zheng, Meng Dou, Lian-Gang Zhuo, Wei Meng and Zhi-Xiang Yu*

*Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering, College of Chemistry, Peking University, Beijing 100871, China, Email:

G.-J. Jiang, Q.-H. Zheng, M. Dou, L.-G. Zhou, W. Meng, Z.-X. Yu, J. Org. Chem., 2013, 78, 11783-11793.

DOI: 10.1021/jo4018183

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1,2,3,4-tetrahydroisoquinoline (THIQ) mediates a practical synthesis of 1,3-disubstituted allenes from terminal alkynes and aldehydes under mild conditions in the presence of CuBr first and then ZnI2. A wide range of aldehydes and terminal alkynes are tolerated, affording the allene products in good yield.

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Key Words


ID: J42-Y2013